Diisobutylaluminumhydride → HCID 17990112, compound

Participants

Reaction Steps

To a solution of THF (40 mL) was added 7 g (13.3 mmol, 1 equiv) of {4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-acetic acid ethyl ester. A 1M solution of diisobutylaluminum hydride in hexanes (53 mL, 53 mmol, 4 equiv) was added to the solution and the reaction was stirred at rt for 3 h. The reaction mixture was quenched with Rochelle's salt followed by EtOAc. The solution was separated and the aqueous layer discarded and the organic layer was washed with brine (100 mL) and water (100 mL). The resulting material 5.5 g (85%)was pure white solid of Example 137. 1H-NMR (DMSO-d6) δ 1.5 (m, 3H), 1.95 (m, 2H), 2.93 (dd,1H), 3.16 (2H), 3.53 (m,2H), 4.45 (t, 1H), 5.2 (s, 2H), 7.17 (m, 2H), 7.28 (m,2H), 7.43 (m, 1H), 7.5 (dd, 2H), 7.76 (dd, 1H), 8.05 (s, 1H). LCMS RT=3.46 min; [M+H]+=484.2.

Provenance & Evidence