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HazMat fee for 500 gram (Estimated)
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USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
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Structure of 1824-81-3 * Storage: {[proInfo.prStorage]}
* 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.
Reference：
[1] Russian Journal of Applied Chemistry, 2005, vol. 78, # 5, p. 787 - 790
2
[ 1824-81-3 ]
[ 39745-39-6 ]
Reference：
[1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[2] Patent: EP2366691, 2011, A1,
3
[ 1824-81-3 ]
[ 532-55-8 ]
[ 96938-51-1 ]
Yield
Reaction Conditions
Operation in experiment
80%
for 3 h; Reflux
To the solution of benzylisothiocyanate (83.0 g, 509.3 mmol) in acetone (700mL) was added compound 6-methylpyridin-2 -amine (50 g, 463.0mmol) in acetone (600 ml) dropwise, then the reaction mixture was stirred at reflux for 3h. The reaction mixture was poured on to crushed ice, then filtered and washed with water, water/MeOH (1 : 1) and MeOH to give l-benzoyl-3-(6- methylpyridin-2-yl)thiourea as a yellow solid (100.1 g, yield 80percent). To a solution of 1-benzoyl-3-(6-methylpyridin-2-yl)thiourea (60 g,221.4 mmol) in THF ( 1000 ml) was added 2N NaOH (243.5ml), then heated at reflux for 3 h. Cooled to RT and filtered to give (6-methylpyridin-2- yl)thiourea as a white solid (34.1 g, yield 92percent). A mixture of (6-methylpyridin-2-yl)thiourea (13.2 g, 79.16 mmol) and 2-bromo-l-(4-bromophenyl)ethan-l-one (22 g, 79.16 mmol) in ethanol (300 mL) was stirred at reflux for 3h, then concentrated and purified with silica gel column to give N-[4-(4-bromophenyl)-l,3-thiazol-2-yl]-6-methylpyridin-2-amine as a yellow solid (14.3 g,53percent). A solution of N-[4-(4-bromophenyl)-l,3-thiazol-2-yl]-6-methylpyridin-2-amine (5 g. 14.5mmol), Bis(pinacolato)diboron (4.8 g, 18.8mmol), Pd(dppf)2Ci2 (1.2 mg, 1.5mmol) and AcOK (4.3 g, 43.3mmol) in dioxane (100ml) was heated to 80 under 2 overnight. The mixture was evaporated to give (6-methyl-N-{4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-l,3-thiazol-2-yl}pyridin-2-amine). Coupling (200mg) with 2-dimethylamino-4- bromopyridine under standard conditions gave 33 mg from 200 mg of, yellow solid, 17 percent yield.
Reference：
[1] Patent: WO2013/33037, 2013, A2, . Location in patent: Paragraph 0752
[2] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 1, p. 137 - 140
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 3081 - 3085
[4] Patent: WO2005/95345, 2005, A2, . Location in patent: Page/Page column 41
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 634 - 639
[6] ChemMedChem, 2013, vol. 8, # 5, p. 847 - 857
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6385 - 6397
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 8, p. 1366 - 1377
Reference：
[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 156 - 167
6
[ 1824-81-3 ]
[ 75073-11-9 ]
Yield
Reaction Conditions
Operation in experiment
77%
With sulfuric acid; iodine; acetic acid; periodic acid In water at 80℃; for 6 h;
To a stirred solution of 6-methyl-pyridin-2-ylamine (30g, 278mmol, 1 eq) in acetic acid (167ml_) was added periodic acid (12.7g, 55.6mmol, 0.2eq) followed by addition of sulphuric acid (4.8ml_, 90.8mmol, 0.34eq), water (33ml_) and iodine (28.7g, 1 1 1 mmol, 0.4eq) at room temperature. Resulting reaction mixture was heated at 80°C for 6 hours. After complete consumption of starting material, reaction mixture was cooled and poured into sodium thiosulfate solution (200ml_), reddish oil was settled down at the bottom. Reaction mixture was decanted from reddish oil, and filtrate was basified with 50percent sodium hydroxide solution (100ml_), yellow colored solid was formed. Resulting solid was extracted with diethyl ether (2 x 200ml_) and dried over sodium sulfate. Organic layer was concentrated under reduced pressure to afford brown semi solid (60g, crude). Crude was purified by column chromatography using silica gel (100-200 mesh). Desired compound was eluted at 15percent EtOAc in hexane to get title compound as faint brown solid (50g, 77percent). H NMR (400 MHz, CDCI3)8: 2.52 (s, 3H), 4.43(bs, 2H), 6.09 (d, J = 8.4 Hz, 1 H), 7.65 (d, J = 8.44 Hz, 1 H). LC-MS (m/z): 235.3 (M+H).
38%
With sulfuric acid; iodine; acetic acid In water
PREPARATION 2 2-amino-5-iodo-6-picoline A mixture of 2-amino-6-picoline (5.40 g), periodic acid (2.28 g), and iodine (5.00 g) is heated in a solution of acetic acid (30 mL), water (6 mL), and sulfuric acid (0.9 mL) at 80° C. for 3 h. The reaction is cooled to room temperature and poured into 100 mL 10percent aqueous sodium bisulfite. The aqueous solution is extracted with diethyl ether (3*100 mL). The combined organics are washed with 10percent NaOH, then dried over Na2SO4, filtered, and concentrated. Purification by chromatography (eluent EtOAc) affords a yellow liquid. The liquid is further dried on the vacuum pump where it crystallizes to afford 2-amino-5-iodo-6-picoline (4.48 g, 38percent). Physical characteristics are as follows: 1H NMR (300 MHz, DMSO-d6) δ 7.60, 6.09, 6.05, 2.38.
7.5 g
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃;
(A) 5-iodo-6-methylpyridin-2-amine (0307) To a solution of 6-methylpyridin-2-amine (10 g, 0.092 mol) in DMF (50 mL) was added N-iodosuccinimide (15 g, 0.13 mol), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (200 mL), and the precipitated solid was collected by filtration and washed with ethyl acetate to give the title compound (7.5 g). MS: [M+H]+ 235.0
With ferrous(II) sulfate heptahydrate; sulfuric acid; boric acid; In water; glycerol; at 0 - 135℃; for 4h;
Sodium-3-nitrobenzenesulfonate (17.5 g, 77.7 mmol), boric acid (2.4 g, 38.8 mmol), and ferrous sulfate heptahydrate (1.4 g, 0.5 mmol) were added to 23.1 mL of 98percent sulfuric acid. After cooling to 0 °C, glycerol (12.5 mL), 2-amino-6-methylpyridine (4.3 g, 40.0 mmol), and hot water (50 °C, 22.5 mL) were slowly added to above mixture. The reaction solution was refluxed for 4 h at 135 °C and cooled to room temperature. 40percent water solution of NaOH was used to mediate pH to 7 and chloroform was used to extract the product. The organic phase was concentrated in vacuum to give the crude product and the final product was obtained by column chromatography (200-300 mesh, 3/1 ethyl acetate/petroleum ether) (3.0 g, 25.9percent yield). Characterization of 2-methyl-1,8-naphthyridine: HRMS (EI) m/z: calcd for C9H9N2 [M+H]+, 145.0766; found, 145.0768. 1H NMR (400 MHz; CDCl3; TMS) 9.08 (d, 1H), 8.13-8.16 (m, 1H), 8.08 (d, 1H), 7.43-7.45 (m, 1H), 7.28 (d, H), 2.82 (s, 3H). 13C NMR: deltaC (100 MHz, CDCl3): 163.1, 160.0, 153.3, 136.9, 136.7, 123.0, 121.4, 120.8, 25.7.
With ferrous(II) sulfate heptahydrate; sulfuric acid; boric acid; sodium 3-nitrobenzenesulfonate; In water; at 50 - 135℃;Cooling with ice; Reflux;
Ice bath under conditions of 250 mLOf the three bottles by adding concentrated H2SO441 g (22 mL),Stir by addingSodium nitrobenzene sulfonate17.5 g (78 mmol),Boric acid2.4 g (39 mmol),FeSO4 · 7H2O 1.4 g (5 mmol)Glycerol 12.5 mL,2-amino-6-methylpyridine (4.3 g, 40 mmol)Mixed evenly after adding 22.5mL 50 warm water,in135 ° CUnder reflux2-3h,After cooling; with 50percent NaOH solution transferred to alkaline, filter,The aqueous solution was extracted three times with chloroform and the organic layer was dried over anhydrous MgSO4,The solvent was removed by rotary distillation to give the crude product which was recrystallized from cyclohexane to give 2-methylnaphthyridine,Ie probe reagent;The concentrated sulfuric acid concentration is 95-98percent;
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