Ammonia → 2-Amino-4-fluoro-6-trifluoromethoxypyrimidine

HRID 1197411Notes

Reaction equation

[NH3:1].F[C:3]1[N:8]=[C:7]([F:9])[CH:6]=[C:5]([O:10][C:11]([F:14])([F:13])[F:12])[N:4]=1>C(OCC)C>[NH2:1][C:3]1[N:8]=[C:7]([F:9])[CH:6]=[C:5]([O:10][C:11]([F:14])([F:13])[F:12])[N:4]=1

Participants

Conditions

Temperature: -70 °C

Procedure

At -75° to -70° C. and over a period of 1 hour, 8.7 g (0.51 mol) of gaseous ammonia was gassed, while stirring, into a mixture of 51 g (0.255 mol) of 2,4-difluoro-6-trifluoromethoxypyrimidine in 200 ml of diethyl ether. The mixture was stirred for 1 1/2 hours at -70° C. and for 1 hour at room temperature. The reaction mixture was evaporated down under reduced pressure, taken up in methylene chloride and extracted with water. The organic phase was dried, evaporated down and chromatographed over silica gel (8:1 ligroin/ether mixture) to give 38.1 g (75.6% of theory) of the title compound as colorless crystals of melting point 86°-89° C.

Workup

customThe reaction mixture was evaporated down under reduced pressure
extractionextracted with water
customThe organic phase was dried
customevaporated down
customchromatographed over silica gel (8:1 ligroin/ether mixture)

Sources & evidence

ORD record: ord-552ebd0b3ea642679ece40248e32c2a2
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05276007

Reaction notes

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