N,N-Dimethylaniline → 4-Chloro-6-cyclopentylpyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-amino-6-cyclopentyl-3H-pyrimidin-4-one (1.52 g, 8.4 mmol), tetraethyl ammonium chloride (2.8 g 16.9 mmol) and dimethylaniline (1.1 mL, 8.4 mmol) in acetonitrile (16 mL) was treated with phosphorous oxychloride (4.7 mL, 51 mmol) and heated at 110° C. for 20 min. The resulting solution was cooled to rt and concentrated to minimum volume then diluted with CHCl3 and ice and stirred for 30 min. The layers were separated and the organic layer was washed with water (3×50 mL) and 5% NaHCO3, dried, and concentrated to yield 2.0 g of crude product that was used without purification.

Provenance & Evidence