N,N-Diethylaniline → HCID 18456543, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 232 mg (0.6 mmol) of 7-benzyl-2-[6-(trifluoromethyl)pyridin-3-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ol from Step A and 1.0 mL of phosphorous oxychloride in a 25-mL round bottom flask was treated with 90 mg (0.095 mL, 0.6 mmol) of N,N-diethylaniline. The mixture was warmed to 110° C. After 4 h, it was cooled to ambient temperature and concentrated in vacuo. Water (15–20 mL) was added. The mixture was neutralized by the addition of solid sodium bicarbonate and extracted with 2 portions of ethyl acetate. The combined organic phases were washed with brine, dried, and concentrated. Purification by flash chromatography (silica gel, 0 to 20% ethyl acetate/hexane step gradient) gave 220 mg of a light yellow oil. LC-MS 405.2 (M+1).

Provenance & Evidence