Triethylamine → HCID 5328400, compound

Participants

Reaction Steps

4-([R]-1-Phenylethylamino)benzothieno[3,2-d]pyrimidine 4-Chlorobenzothieno[3,2-d]pyrimidine (110.1 mg, 0.5 mmol), [R]-1-phenylethylamine (74 mg, 0.6 mmol) and NEt3 (111 mg, 1.1 mmol) in stirred propanol (2 mL) are heated at reflux under N2 for 9 h. The mixture is allowed to cool, and is then purified by preparative tlc on silica, eluting once with 2% MeOH in CHCl3. The yellow solid is recrystallized from EtOH at 0° C. to give 4-([R]-1-phenylethylamino)benzothieno[3,2-d]pyrimidine, (75 mg, 49%) as pale yellow cubic crystals. 1H NMR (DMSO) δ8.53(1H, s), 8.30(1H, d, J=7.2 Hz), 8.15 (1H, d, J=8.2 Hz), 7.68 (1H, dt, Jd=1.2 Hz, Jt=7.5 Hz), 7.58 (1H, dt, Jd=1 Hz, Jt=7.5 Hz), 7.44 (1H, dd, J=1, 8 Hz), 7.31 (2H, t, J=7.7 Hz), 7.21 (1 H, tt, J=1, 7.7 Hz), 5.58(1H, q, J=7 Hz), 1.58 (3H, d, J=7 Hz).

Provenance & Evidence