N,N-Dimethylaniline → 4-Chloro-6-(trifluoromethyl)pyrimidin-2-amine

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.O=P(Cl)(Cl)[Cl:15].CN(C)C1C=CC=CC=1>>[Cl:15][C:6]1[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

Reactant 3

HCID 949N,N-Dimethylaniline

HCID 24813Phosphorus oxychloride

HCID 178508973HCID 178508973, compound

Product 1

HCID 130869074-Chloro-6-(trifluoromethyl)pyrimidin-2-amine

Conditions

Temperature: 70 °C

Procedure

2-Amino-6-(trifluoromethyl)pyrimidin-4-ol (200 mg, 1.1 mmol) is dissolved in POCl3 (3 eq., 0.3 mL, 3.3 mmol) and dimethylaniline (0.28 mL, 2 eq.) is added. The reaction mixture is heated at 70° C. for 4 h. The resulting mixture is poured into a mixture of ice-water, and the resulting precipitate is collected to yield the desired compound 24 in 59%. ESI-MS m/z 198 [M+H]+.