Water → Methyl N-(4-methylpyridin-3-yl)carbamate

HRID 1506190Notes

Reaction equation

CC(C)([O-])C.[K+].[C:7](=[O:12])(OC)[O:8][CH3:9].[NH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20].O>O1CCCC1>[CH3:20][C:19]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH:13][C:7](=[O:12])[O:8][CH3:9]

Participants

Conditions

Temperature: 17.5 °C

Procedure

Potassium tert-butoxide (10.3 g, 92.5 mmol) in tetrahydrofuran (25 mL) was stirred at 23 to 27° C. for 30 minutes, and dimethyl carbonate (4.67 mL, 55.5 mmol) was added while the temperature was kept at 35° C. or below. To the reaction mixture, 3-amino-4-methylpyridine (5.00 g, 46.2 mmol) in tetrahydrofuran (40 mL) stirred at 32 to 38° C. for 90 minutes was added dropwise at 20 to 35° C. over 2 hours with stirring. The resulting reaction mixture was cooled to 15 to 20° C., stirred with water (25 mL) at 25° C. or below for 1 hour and extracted with tetrahydrofuran. The organic layer was azeotropically distilled with toluene under reduced pressure to a volume of about 50 mL and stirred at 23 to 27° C. for one day. The precipitated solid was collected by filtration, washed with toluene and dried under reduced pressure to give the title compound as a brown solid (6.77 g, yield 88%).

Workup

customwas kept at 35° C. or below
additionwas added dropwise at 20 to 35° C. over 2 hours
customThe resulting reaction mixture
extractionextracted with tetrahydrofuran
distillationThe organic layer was azeotropically distilled with toluene under reduced pressure to a volume of about 50 mL
stirringstirred at 23 to 27° C. for one day
filtrationThe precipitated solid was collected by filtration
washwashed with toluene
customdried under reduced pressure

Sources & evidence

ORD record: ord-ef8142deca094bfc9a6e6550347246a7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216999B2

Reaction notes

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