N,N-Dimethylaniline → 4-Chloro-2-(trifluoromethyl)pyrimidine

Temperature

110 °C

N,N-Dimethylaniline (6.06 mmol. 2.3 eq.) was added dropwise to a stirring solution of 2-(trifluoromethyl)pyrimidin-4-ol (2.72 mmol, 1 eq.) in POCl3 (4 ml) and the reaction mixture was stirred at 110° C. for 2 h. The reaction mixture was concentrated and the brown liquid was diluted with cold water (50 ml) and rendered basic with saturated sodium carbonate solution (50 ml). The mixture was extracted with methylene chloride (3×100 ml) and the combined organic phases were washed with water (2×50 ml) and sat. NaCl solution (50 ml) and dried over sodium sulfate. After concentration on a rotary evaporator, a blue liquid remained, which was employed in the next step without purification.

1. concentrationThe reaction mixture was concentrated
2. additionthe brown liquid was diluted with cold water (50 ml)
3. extractionThe mixture was extracted with methylene chloride (3×100 ml)
4. washthe combined organic phases were washed with water (2×50 ml) and sat. NaCl solution (50 ml)
5. dry with materialdried over sodium sulfate
6. concentrationAfter concentration
7. customon a rotary evaporator
8. customwhich was employed in the next step without purification

ORD record

ord-119ae52725ae4583b98337b69b3ad962

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455475B2