Ammonia → HCID 178507981, compound

HRID 232519Notes

Reaction equation

HRID 232519 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

Procedure

4.3 g (0.25 mol) of gaseous ammonia were passed into a mixture of 23.3 g (0.1 mol) of 2,4-dichloro-6-trifluoromethoxypyrimidine in 150 ml of methyl tert-butyl ether in the course of 45 minutes while stirring at -50° to -45° C. Stirring was continued for 30 minutes at -50° C., for 1 hour at -30° C. and for 1 hour at 25° C. The precipitate which separated out was filtered off under suction, washed with water and dried, 5.4 g (33.1% of theory) of 4-amino-2,4-dichloropyrimidine of melting point 270°-272° C. being obtained as a byproduct. The filtrate was washed with water, dried, partially evaporated down under reduced pressure and subjected to fractional chromatography using 5:1 petroleum ether/ether, 3 g (12.8% of theory) of starting material being obtained as a colorless oil from the first fractions and 9 g (42% of theory) of the title compound being obtained as colorless crystals of melting point 55°-56° C. from the final fraction. The conversion was 48.3%.

Workup

  1. stirringStirring
  2. customThe precipitate which separated out
  3. filtrationwas filtered off under suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e348d96423e3430c8de2b4aba9f34eb4
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

Loading…