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With iodine; sodium carbonate; potassium iodide In water for 7 h; Reflux
5-iodo-2-methylpyridin-4-amine (i55): To a solution of 2-methylpyridin-4-amine (5 g, 46 mmol) in water (25 ml_), Na2C03 (3.4 g, 32 mmol) was added and the reaction mixture was refluxed. Kl (9.8 g, 59 mmol) and l2 (9.3 g, 36 mmol in 50 mL water) were added and refluxed for 7h. The reaction mixture was quenched with sodium thiosulphate solution and the compound was extracted with DCM. The organic layer was separated dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was purified by silica gel (100:200 mesh) column chromatography using 25percent ethyl acetate in hexane as eluent to afford desired product 5-iodo-2-methylpyridin-4-amine (i55) (0.85 g, Yield 8percent). 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 6.00 (s, 2H), 6.49 (s, 1 H), 8.22 (s, 1 H). MS (ESI) m/e (M+1 )+: 235
With iodine; sodium carbonate; potassium iodide In water for 2 h; Heating / reflux
A solution OF 2-METHYL-4-NITROPYRIDINE-N-OXIDE (3.80 g, 24.6 mmol) in 100 ML of acetic acid was slowly heated with iron powder (6.89 g, 124 mmol) in a large flask (caution: the reaction becomes very exothermic upon turning brown). The resulting slurry was heated for 2 hours at 80 C. Excess acetic acid was removed IN VACUO, THE residue was taken up in 20percent aqueous sodium hydroxide solution, and 100 mL of chloroform (CHC13) was added and the mixture filtered through CELITES FILTER aid. The aqueous phase was extracted with two 200 mL portions of chloroform. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product (2.2 g, 83percent yield) was used without further purification. A solution OF KI (1. 96 g, 11. 9 mmol) and 12 (1.87 g, 7.36 mmol) in 10 ML of water was added to a REFLUXING solution of the 2-methylpyridin-4-ylamine (1.00 g, 9.25 mmol) and sodium carbonate (683 mg, 6.44 mmol) in 5 ML of water. The mixture was heated at reflux for 2 hours, cooled to room temperature, and treated with 20 mL of ethyl acetate (EtOAc). Phases were separated and the aqueous layer was extracted with three 20 ML portions of ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium thiosulfate (NA2S203) solution, dried over magnesium sulfate, and concentrated ILL vacuo. Flash chromatography (30percent ethyl acetate in hexanes to 100percent ethyl acetate, gradient) of the resulting residue yielded 4-amino-3-iodo-6-methylpyridine (first eluting: 226 mg, 11percent yield) and 4- AMINO-3-IODO-2-METHYLPYRIDINE (second eluting : 116 mg; 5percent yield).
With palladium 10% on activated carbon; hydrogen; In methanol; at 30℃; under 3750.38 Torr; for 15h;Autoclave;
2-methyl-4-nitropyridine (13.8 g, 0.1 mol) was dissolved in a methanol solution.10% Pd/C (0.1 g) was added, and the reaction was carried out in an autoclave, and hydrogen gas was passed to a pressure of 0.5 MPa, and the temperature was raised to 30 C for 15 hours.TLC was monitored until the reaction was complete, cooled to room temperature, diatomaceous earth was filtered, and the filter cake was washed with dichloromethane.This prevents Pd/C from catching fire and the filtrate is concentrated to give 2-methyl-4-aminopyridine.The molar yield was 97%.
97%
With palladium 10% on activated carbon; hydrogen; In methanol; at 30℃; under 3750.38 Torr; for 15h;Autoclave;Catalytic behavior;
Dissolve 2-methyl-4-nitropyridine (13.8g, 0.1mol) in methanol solution,10% Pd / C (0.1g) was added and the reaction was carried out in an autoclave,Hydrogen was passed to a pressure of 0.5 MPa, the temperature was raised to 30 C, and the reaction was carried out for 15 hours.TLC monitoring until the reaction is complete, cooled to room temperature, diatomite filter aid,The filter cake is washed with dichloromethane to prevent Pd / C from catching fire.The filtrate was concentrated to give 2-methyl-4-aminopyridine in a molar yield of 97%.
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