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

HRID 2254848Notes

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

8.7 g (0.51 mol) of gaseous ammonia were passed over the course of 1 hour into a stirred mixture of 51 g (0.255 mol) of 2,4-difluoro-6-trifluoromethoxypyrimidine and 200 ml of diethyl ether at -75° to -70° C. The mixture was stirred at -70° C. for 11/2 hours and at room temperature for 1 hour and then concentrated under reduced pressure. The residue was taken up in methylene chloride and the organic phase was extracted with water, dried, concentrated and chromatographed on silica gel with 8:1 petroleum ether/ether, resulting in 38.1 g (75.6% of theory) of the title compound as colorless crystals of melting point 86°-89° C.

Workup

waitat room temperature for 1 hour
concentrationconcentrated under reduced pressure
extractionthe organic phase was extracted with water
customdried
concentrationconcentrated
customchromatographed on silica gel with 8:1 petroleum ether/ether

Sources & evidence

ORD record: ord-12af0bc987d343f5b646aefed47a0fc9
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05237063

Reaction notes

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