Hydrochloric Acid → 2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (1.0 g, 3.91 mmol) in anhydrous THF (50 mL) was added N,N,N′,N′-tetramethylethylenediamine (0.68 mL, 4.53 mmol) and the resulting mixture was cooled to −78° C. n-Butyl lithium (2.5 M in hexanes, 1.9 mL, 4.75 mmol) was added dropwise and the resulting suspension allowed to warm to −30° C. over 1 h. The reaction mixture was cooled to −78° C. and treated with DMF (0.7 mL, 9.04 mmol), then stirred at RT for 30 min. The reaction mixture was cooled to 0° C. before an aqueous solution of HCl (0.5 M) was added and the mixture stirred for another 30 min. The precipitate that formed was collected by filtration, washed twice with water then dried in vacuo at 70° C. for 3 h. The title compound was obtained as a pale yellow solid (1.0 g 90%).

Provenance & Evidence