Diisobutylaluminum hydride → N-(3-bromophenyl)-7-(1-piperidinylmethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

Anhydrous THF (3 mL) was added to a 50 mL round bottom flask followed by N-(3-bromophenyl)-7-(1-piperidinylcarbonyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine (27, 0.21 mmol, 1equiv). This was cooled to 0° C. in an ice-water bath for 5 min. Diisobutylaluminum hydride, 0.6 mL (DIBAL-H, 0.64 mmol, 1.0M in THF) was added and the reaction was stirred at 0° C. for 30 min before warming to rt for 2 h until reaction was complete by TLC. The reaction mixture was quenched with a satd solution of Rochelle's salt (3 mL) followed by water (3 mL). The reaction was extracted with EtOAc (3×10 mL). The organic layer was dried over anhyd Na2SO4 and concentrated to give a crude oil which was purified via flash column chromatography MeOH/CH2Cl2 1:9 w/0.5% NH4OH to provide the required product, 30, as an oil (70 mg, 72%). 1H-NMR (CD2Cl2-d4) δ 8.36 (s, 1H), 7.94 (t, 1H), 7.50–7.47 (m, 1H), 7.15–7.13 (m, 2H), 7.10 (s, 1H), 2.95–2.91 (m, 3H), 2.29–2.05 (m, 7H), 1.52–1.47 (m, 5H), 1.36 (t, 1H); LCMS RT=2.36 min; [M+H]+=459.2.

Provenance & Evidence