Ammonia → HCID 178507981, compound

HRID 1197412Notes

Reaction equation

HRID 1197412 reaction equation
[NH3:1].[Cl:2][C:3]1[N:8]=[C:7]([Cl:9])[CH:6]=[C:5](OC(F)(F)F)[N:4]=1>C(OC)(C)(C)C>[NH2:1][C:7]1([Cl:9])[CH:6]=[CH:5][N:4]=[C:3]([Cl:2])[NH:8]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15022714HCID 15022714, compound

Product 1

HCID 178507981HCID 178507981, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

At -50° to -45° C. and over a period of 45 minutes, 4.3 g (0.25 mol) of gaseous ammonia was passed, while stirring, into a mixture of 23.3 g (0.1 mol) of 2,4-dichloro-6-trifluoromethoxypyrimidine in 150 ml of methyl tert-butyl ether. The mixture was stirred for 30 minutes at -50° C., 1 hour at -30° C. and for 1 hour at 25° C. The precipitate was suction filtered, washed with water and dried, giving 5.4 g (33.1% of theory) of 4-amino-2,4-dichloropyrimidine of melting point 270°-272° C. as byproduct. The filtrate was washed with water, dried, evaporated down partially under reduced pressure, and fractionally chromatographed with a 5:1 ligroin/ether mixture, the first fractions giving 3 g (12.81% of theory) of the starting material as a colorless oil and the last runnings 9 g (42% of theory) of the title compound as colorless crystals of melting point 55°-56° C. The conversion was 48.3%.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-a05685c028ad49d49d080c1e8b89b785
Source dataset
uspto-grants-1994_01
Patent number
US05276007

Reaction notes

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