Water → 6-Bromo-4-chlorothieno(3,2-d)pyrimidine

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round-bottomed flask 65 mL of tetrahydrofuran and lithium diisopropylamine (18.5 mL, 37 mmol, 2M in tetrahydrofuran) were cooled to −78° C. 4-chloro-thieno[3,2-d]pyrimidine (5.26 g, 31 mmol) was dissolved in 37 mL of tetrahydrofuran and slowly added to the reaction mixture over 5 minutes, After 20 minutes 1,2-dibromo-1,1,2,2-tetrafluoroethane (4.05 mL, 34 mmol) was added slowly to the solution of the anion. The temperature was maintained at −78° C. for 20 minutes then warmed to room temperature for 2 hours. The reaction mixture was poured into water and extracted with chloroform (3×100 mL), dried over sodium sulfate, and dried in vacuo to afford 7.70 g (99%) of 6-bromo-4-chloro-thieno[3,2-d]pyrimidine. 1H NMR (400 MHz, DMSO) d 8.97 (s, 1H), 8.01 (s, 1H). LC-MS: 249, 251 (MH+); HPLC RT: 4.04 minutes.

Provenance & Evidence