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

Temperature

-30 °C

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%).

1. additionwas added dropwise
2. temperatureThe reaction mixture was cooled to −78° C.
3. additionwas added
4. stirringthe mixture stirred for another 30 min
5. customThe precipitate that formed
6. filtrationwas collected by filtration
7. washwashed twice with water
8. customthen dried in vacuo at 70° C. for 3 h

ORD record

ord-ca687c8a8ceb416095ca1dcc5cb6df91

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293735B2