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

HRID 1974648Notes

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 9 (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-ddd9c55e7ea14df186998bbc8fed8eb3
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283332

Reaction notes

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