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[ CAS No. 5909-24-0 ] {[proInfo.proName]}

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Chemical Structure| 5909-24-0
Chemical Structure| 5909-24-0
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Product Details of [ 5909-24-0 ]

CAS No. :5909-24-0 MDL No. :MFCD00006085
Formula : C8H9ClN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :SNNHLSHDDGJVDM-UHFFFAOYSA-N
M.W : 232.69 Pubchem ID :80008
Synonyms :

Calculated chemistry of [ 5909-24-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.85
TPSA : 77.38 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 2.26
Consensus Log Po/w : 1.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.423 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0753 mg/ml ; 0.000323 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.129 mg/ml ; 0.000556 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 5909-24-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5909-24-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5909-24-0 ]

[ 5909-24-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 53554-29-3 ]
  • [ 5909-24-0 ]
YieldReaction ConditionsOperation in experiment
92% With thionyl chloride; at 60℃; for 3h; Ethyl 4-hydroxy-2-methylthiopyrimidine-5-carboxylate (30 g, 140 mmol) was added to a three-vial flask.Add 20g of thionyl chloride (168mmol)The reaction was heated to 60C for 3 hours. After the reaction was complete, it was cooled to 0-5C. 100 ml of water was added and crystallized at 0-5C for 1-2 hours. The mixture was filtered and vacuum dried at 50C to give 30.1 g of white solid product. Yield 92 %, pure 99.8%,
77% With N,N-diethylaniline; trichlorophosphate; for 5h;Heating / reflux; A mixture of 4-hydroxy-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (50 g, 0.234 mmol), POC13 (110 mL, 1.17 mmol) and diethylamide (70 mL, 0.28 mmol) was refluxed for 5h. The solvent was removed under vacuum and the residue was dissolved in ice H2O and cautiously neutralized with aqueous NaHCO3. After extraction with EtOAc (3x400 mL), the organic extracts were combined, dried and concentrated to give 4-chloro-2- (methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester as a yellow solid (42 g, 77% yield).
77% With trichlorophosphate; In acetonitrile; for 6h;Reflux; the ethyl 4-hydroxy-2-methylsulfanyl-5-carboxylate obtained in the step S1 (55.6 g, 0.26 mol) was added to 150 mL of acetonitrile.Stir for 25min,Slowly add 135 mL of POCl3 to the reaction solution.After the addition is completed,The reaction solution was heated to reflux for 6 h.Then the reaction solution is slightly cold,The reaction solution was concentrated and the residue was poured into an ice water mixture and stirred.Adjust the pH of the reaction solution to neutral with saturated sodium bicarbonate solution.When a large amount of white solid precipitates, suction filtration is performed.The filter cake is used in turn (135mL × 3),Anhydrous ethanol (30 mL × 3) was rinsed.Then dried in vacuo to give a white solid (47.8 g, 77%);
40% With trichlorophosphate; at 10 - 65℃; for 7h; Step 2. Preparation of 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (B19-2): Neat POCl3 (120 mL) was cooled to 10 C. and treated portion-wise over 4 hours with B19-1 (50 g, 232 mmol) without exceeding a temperature of 25 C. The mixture was then heated at 65 C. After 3 hours the mixture was cooled to 10 C., poured into crushed ice (350 g), treated drop-wise with water (676 mL) under vigorous stirring. The resultant solids were collected and dried under reduced pressure to provide B19-2 as a pale yellow solid. Yield: 22 g, 40%. 1H NMR (CDCl3): delta 8.95 (s, 1H), 4.44 (q, 2H), 2.62 (s, 3H) and 1.42 (t, 3H).
With trichlorophosphate; In toluene; at 55 - 105℃; for 4h; The wet solid obtained in step-a) was dissolved in toluene (800 ml) by heating the reaction mixture to 85-90C. The reaction mixture was kept aside for 15 minutes and both the organic and aqueous layers were separated. The organic layer was heated to 110-115C to remove water from it. Cooled the reaction mixture to 55-60C. Phosphoryl chloride (106.36 g) was added to the organic layer at 55-60C, heated the reaction mixture to 100-105C and then stirred for 4 hours. The reaction mixture was cooled to 0-5C and then quenched with water at a temperature below 40C. The reaction mixture was heated to 40-45 C and separated both the organic and aqueous layers. The organic layer was washed with 5% sodium carbonate solution followed by water. The organic layer containing the title compound is taken to the next step.

  • 2
  • [ 5909-24-0 ]
  • [ 21075-86-5 ]
  • [ 955368-90-8 ]
YieldReaction ConditionsOperation in experiment
51% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 72h;Reflux; DIPEA (20.8 ml, 120 mmol) and allyl hydrazine 5 (8.23 g, 47.8 mmol) were added to a solution of ethyl 4-chloro-2-methylthio- 5-pyrimidinecarboxylate (6; 1 1.1 g, 47.8 mmol) in THF (150 ml). The reaction mixture was heated at reflux for 72 h, before being concentrated in vacuo. Et20 (50 ml) was added to the residue, and the resultant precipitate was collected by filtration. The filtrate was evaporated to dryness, and the residue was cooled in an ice bath, after which TFA (40 ml) was added. The resultant solution was stirred at RT for 1 h, followed by 70 C for 1 h. The solvent was removed in vacuo and the residue was dissolved in EtOH (50 ml) and cooled in an ice bath, after which 6M NaOH (75 ml) was added. The resultant solution was stirred at RT for 15 min, before 32 being acidified via the addition of cone. HCI (40 ml). The orange solution was evaporated to dryness and the resultant residue was partitioned between chloroform (100 ml) and water (100 ml), and the organic phase was washed with brine (50 ml), dried (Mg2S04), concentrated in vacuo, and triturated with hexanes. The solid precipitate was washed with EtOH and Et20, before being dried under vacuum to give the target compound as a yellow solid (5.44 g, 24.5 mmol, 51 %). Rf 0.45 (9:1 DCM:MeOH); M.p. 125- 128 C; IR (cm-1 ) 3032, 2979, 2926, 2659, 1656, 161 5, 1 566, 1 514; 1 H NMR (400 M Hz, DMSO-d6)2.53 (3H, s, -SCH3), 4.38 (2H, dapp, J = 5.2 Hz, N2-CH2), 5.06-5.20 (2H, m, allyl C-Hcis/trans), 5.87 (1 H, ddt, J = 17.2, 10.5, 5.3 Hz, alkene C-H), 8.67 (1 H, s, H-4), 12.65 (1 H, -1 ); MS [M + H] + m/z 223.1.
260 mL of N,N-diisopropylethylamine and 106 g of the hydrazine obtained in the above 1 were added to tetrahydrofuran (1.5 L) solution of 142 g of ethyl 4-chloro-2-(methylthio)pyridine-5-carboxylate, and stirred with heating under reflux for 18 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, and 500 mL of diethyl ether was added to the residue, and the precipitated solid was separated through filtration. The filtrate was evaporated under reduced pressure, the residue was cooled in an ice bath, 400 mL of trifluoroacetic acid was gradually added thereto, and stirred at room temperature for 1 hour and then at 70 C. for 1 hour. The reaction solution was evaporated under reduced pressure, 500 mL of ethanol was added thereto and cooled in an ice bath, and 1.0 L of 6 N sodium hydroxide solution was added thereto and stirred at room temperature for 15 minutes. Cooled in an ice bath, the reaction solution was made acidic with 400 mL of concentrated hydrochloric acid, and then evaporated under reduced pressure. The residue was partitioned in chloroform and water, and the chloroform layer was extracted, washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the formed yellow solid was taken out through filtration, washed with ethanol and diethyl ether, and dried to obtain 99.1 g of the entitled compound as a yellow solid.1H-NMR (400 MHz, DMSO-d6) ?: 8.66 (1.0H, brs), 5.83 (1.0H, ddt, J=17.1, 9.8, 5.4 Hz), 5.13 (1.0H, d, J=9.8 Hz), 5.06 (1.0H, d, J=17.1 Hz), 4.34 (2.0H, d, J=5.4 Hz), 2.51 (3.0H, s).ESI-MS Found: m/z[M+H]+ 223.3.
2) Production of 2-allyl-6-(methylthio)-l ,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one:260 mL of N,N-diisopropylethylamine and 106 g of the hydrazine obtained in the above 1 were added to tetrahydrofuran (1.5 L) solution of 142 g of ethyl 4-chloro-2- (methylthio)pyridine-5-carboxylate, and stirred with heating under reflux for 18 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, and 500 mL of diethyl ether was added to the residue, and the precipitated solid was separated through filtration. The filtrate was evaporated under reduced pressure, the residue was cooled in an ice bath, 400 mL of trifluoroacetic acid was gradually added thereto, and stirred at room temperature for 1 hour and then at 70C for 1 hour. The reaction solution was evaporated under reduced pressure, 500 mL of ethanol was added thereto and cooled in an ice bath, and 1.0 L of 6 N sodium hydroxide solution was added thereto and stirred at room temperature for 15 minutes. Cooled in an ice bath, the reaction solution was made acidic with 400 mL of concentrated hydrochloric acid, and then evaporated under reduced pressure. The residue was partitioned in chloroform and water, and the chloroform layer was extracted, washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the formed yellow solid was taken out through filtration, washed with ethanol and diethyl ether, and dried to obtain 99.1 g of the entitled compound as a yellow solid. iH-NMR (400 MHz, DMSO-d6) delta: 8.66 (1.0H, brs), 5.83 (1.0H, ddt, J=17.1, 9.8, 5.4 Hz), 5.13(l.OH, d, J=9.8 Hz), 5.06 (1.0H, d, J=I 7.1 Hz), 4.34 (2.0H, d, J=5.4 Hz), 2.51 (3.0H, s). ESI-MS Found: m/z[M+H]+ 223.3.
260 mL of N,N-diisopropylethylamine and 106 g of the hydrazine obtained in the above 1 were added to tetrahydrofuran (1.5 L) solution of 142 g of ethyl 4-chloro-2- (methylthio)pyridine-5-carboxylate, and stirred with heating under reflux for 18 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, and 500 mL of diethyl ether was added to the residue, and the precipitated solid was separated through filtration. (0207) The filtrate was evaporated under reduced pressure, the residue was cooled in an ice bath, 400 mL of trifluoroacetic acid was gradually added thereto, and stirred at room temperature for 1 hour and then at 70C for 1 hour

  • 3
  • [ 5909-24-0 ]
  • [ 211244-81-4 ]
  • 4
  • [ 5909-24-0 ]
  • [ 10519-96-7 ]
  • [ 397308-78-0 ]
YieldReaction ConditionsOperation in experiment
73% A. 4-Chloro-2-methylsulfanylpyrimidine-5-carbonyl chloride A slurry of potassium trimethylsilyl oxide (90% tech., 40 g, 0.31 mol) in 1,2-dimethoxyethane (300 mL) was added, slowly over 20 min, to a solution of ethyl-4-chloro-2-methylthio-5-pyrimidinecarboxylate (Aldrich, 15 g, 64 mmol) in 1,2-dimethoxyethane (100 mL). Said addition, being mildly exothermic, may warrant the use of an ice bath to maintain ambient temperature conditions during addition. After addition was complete, the resulting suspension was stirred at ambient temperature for 1 h, then warmed to reflux for 36 h, then allowed to cool to ambient temperature. Reaction mixture was quenched with 1 M HCl(aq), then extracted with ethyl acetate and dried using sodium sulfate to produce a crude solid (11 g). Said crude solid was then recrystallized in ethyl acetate to afford 4-hydroxy-2-methylsulfanylpyrimidine-5-carboxylic acid as a white solid (8.8 g, 47 mmol, 73% yield). MS (-ESI) m/z 185 (M-, 100). An aliquot of this material (3.00 g, 16.1 mmol) was diluted with thionyl chloride (90 mL) followed by DMF (0.20 mL) and the resulting solution was warmed to reflux. After 1 hour at reflux, the solution was allowed to cool to ambient temperature and was concentrated in vacuo to afford a beige solid which was triturated once from hot toluene and then once again from hot hexanes (i.e., in both instances the soluble material was the desired fraction). This afforded, after concentration in vacuo, the titled compound as a white solid (3.90 g, 15.6 mmol, 97% yield). 1H NMR (300 MHz, CDCl3) delta 9.15 (s, 1H), 2.63 (s, 3H).
  • 5
  • [ 5909-24-0 ]
  • [ 33024-60-1 ]
  • [ 933794-99-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; Example 1: Synthesis of tert-butyl 4-['6-r2-methylphenyl)-7-oxo-8-(tetrahydro-2H'- pyran-4-yl)-7,8-dihvdropyridof2,3-cpipyrimidin-2-yl]ammo}piperidine-l-carboxylate (Compound No. 1) Step a: 2-MethylsuIfanyl-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-5- carboxylic acid ethyl ester; To a suspension of ethyl-4-chloro-2-methylthio-5-pyrimidine carboxylate (commercially available) (3.0 g, 12 mmol) in dry tetrahydrofuran (50 mL) was added triethylamine (2.6 g, 25 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-ylamine hydrochloride</strong> (1.94 g, EPO <DP n="44"/>14 mmol) at room temperature and the mixture was stirred for 4 hours. The organic solvent was evaporated under reduced pressure followed by addition of cold water. The residue thus obtained was filtered, washed with water and dried under vacuum to yield the title compound. Yield = 2.7 g.
  • 6
  • [ 67-56-1 ]
  • [ 5909-24-0 ]
  • [ 84332-06-9 ]
YieldReaction ConditionsOperation in experiment
66.25% With sodium hydroxide; at 20℃; for 3h; To a stirred solution of 5 ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (3.0 g, 12.893 mmol, 1.0 eq), in 30 MeOH (15 mL) was added 1M solution of 8 NaOH (20 mL) at rt. The resulting mixture was stirred at the same temperature for 3 h. The reaction mixture was concentrated and acidified with 1N HCl solution (10 mL) to adjusted the pH 4-5, the formation of white precipitate was observed which was filtered and dried under vacuum to afford the desired compound 426 4-methoxy-2-(methylthio)pyrimidine-5-carboxylic acid (1.71 g, 66.25%) as white solid. (0498) LCMS: 201.1[M+1]+
With sodium hydroxide; at 20℃; for 3h; Weigh ethyl 4-chloro-2-methylthio 5-pyrimidinecarboxylate (2 g, 8.6 mmol) into a 100 mL eggplant-shaped flask, and add 30 mL MeOH and 10 mL 2N NaOH solution sequentially.After stirring at room temperature for 3 hours, most of the methanol was evaporated to dryness, the resulting solution was acidified with 2N dilute hydrochloric acid solution to a pH of 4-5, filtered to obtain a pure white solid, and vacuum dried overnight.Without further purification directly to the next step.
With water; sodium hydroxide; (1) Using ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate as the starting material, the intermediate (I-1) was obtained in methanol and aqueous sodium hydroxide (J.Med.Chem.2009 , 52, 1081-1099).
  • 10
  • [ 5909-24-0 ]
  • [ 397308-78-0 ]
YieldReaction ConditionsOperation in experiment
75% With water; sodium hydroxide; In ethanol; at 110.0℃; for 2h; To a stirred solution of 5 ethyl 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylate (10 g, 43.1 mmol, 1.0 eq) in 150 mL of 6 ethanol: 7 water (2:1) was added 8 NaOH (17.2 g, 431 mmol, 10 eq). Reaction was heated at 110 C. for 2 h. Progress of reaction was monitored by LCMS. Upon the consumption of starting material, solvent was removed under reduced pressure. Residue was diluted with 100 mL of water and pH of mixture was adjusted up to 5 with 3N HCl solution. Precipitated compound was filtered off, washed with water (50 mL) and dried under vacuum to obtain the desired 9 product, 10 4-hydroxy-2-methyl sulfanyl-pyrimidine-5-carboxylic acid (6.0 g, 75%). (0219) LCMS: 187 [M+1]+
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