Ammonia → HCID 15022717, compound

HRID 2254849Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

4.3 g (0.25 mol) of gaseous ammonia were passed over the course of 45 minutes into a stirred mixture of 23.3 g (0.1 mol) of 2,4-dichloro-6-trifluoromethoxypyrimidine and 150 ml of methyl tert.-butyl ether at -50° to -45° C. The mixture was stirred at -50° C. for 30 minutes, at -30° C. for 1 hour and at 25° C. for 1 hour. The precipitate was filtered off with suction, washed with water and dried, resulting in 5.4 g (33.1% of theory) of 4-amino-2,4-dichloropyrimidine of melting point 270°-272° C. as by-product. The filtrate was washed with water, dried and concentrated under reduced pressure, and the residue was chromatographed with 5:1 petroleum ether/ether, the initial fractions yielding 3 g (12.8% of theory) of starting material as a colorless oil, and subsequent fractions containing 9 g (42% of theory) of the title compound as colorless crystals of melting point 55°-56° C. Conversion was 48.3%.

Workup

filtrationThe precipitate was filtered off with suction
washwashed with water
customdried
customresulting in 5.4 g (33.1% of theory) of 4-amino-2,4-dichloropyrimidine of melting point 270°-272° C. as by-product
washThe filtrate was washed with water
customdried
concentrationconcentrated under reduced pressure
customthe residue was chromatographed with 5:1 petroleum ether/ether
customthe initial fractions yielding 3 g (12.8% of theory) of starting material as a colorless oil, and subsequent fractions

Sources & evidence

ORD record: ord-020c8f4064404efa8b7488de89a51930
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05237063

Reaction notes

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