Ammonia → Ammonia methanol

HRID 1725673Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1.[NH3:17]>C(O)CO>[NH3:7].[CH3:9][OH:10].[NH2:17][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A pressure tube was charged with 6-bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine (34) (0.287 g), ethylene glycol (3 mL) and Cu2O (0.028 g) and cooled to −78° C. To this mixture, 1 mL of liquid ammonia was collectyed (at −78° C.), the pressure tube was sealed and then stirred at room temperature for 24 hours. The reaction mixture was again cooled to −78° C., the seal was removed and the reaction mixture diluted with water (10 mL). The aqueous solution was extracted with ethyl acetate (3×50 mL), dried over anhydrous sodium sulfate and solvent was removed under a reduced pressure. The resulting residue was chromatographed (silica gel, CH2Cl2 then 1% 2N NH3/MeOH in CH2Cl2 to obtain 6-amino-2-(tert-butylcarbonyl)amino-3-methoxypyridine (35). LCMS: purity: 94%; MS (m/z): 224 (MH+).

Workup

custom(at −78° C.)
customthe pressure tube was sealed
temperatureThe reaction mixture was again cooled to −78° C.
customthe seal was removed
additionthe reaction mixture diluted with water (10 mL)
extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
dry with materialdried over anhydrous sodium sulfate and solvent
customwas removed under a reduced pressure
customThe resulting residue was chromatographed (silica gel, CH2Cl2

Sources & evidence

ORD record: ord-b6ef1759000c480589cb1f37a9f72728
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491732B2

Reaction notes

Loading…