Dimethylformamide → 4-Chlorothieno[2,3-d]pyrimidine

Participants

Reaction Steps

To a solution of DMF (90 μL) and CH2Cl2 (2 mL) at 0° C. under N2,, oxalyl chloride (148 mg, 1.2 mmol) is added slowly and stirred for 10 min. 3H-Thieno[2,3-d]pyrimid-4-one (81 mg, 0.52 mmol) is added as a solid to the solution and warmed with a heat gun until the solid dissolves. The reaction is stirred at 25° C. for 12 h under N2. The reaction mixture is poured into water and extracted with CH2Cl2. The phases are separated and the organic layer is dried (Na2SO4) and stripped under reduced pressure to yield 4-chlorothieno[2,3-d]pyrimidine (87.6 mg, 97%) as a solid. 1H NMR (DMSO) δ 8.96 (1H, s), 8.17 (1H, d, J=6.0 Hz), 7.62 (1H, d, J=6.0 Hz).

Provenance & Evidence