Diisobutylaluminumhydride → HCID 17989944, compound

Participants

Reaction Steps

To a solution of THF (100 mL) was added 4.50 g (9.04 mmol, 1 equiv) of [4-(1-Benzyl-1H-indazol-5-ylamino)-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 THF (45.2 mL, 45.2 mmol, 5 equiv) was added to the solution at 0° C. and the reaction was stirred for 30 min before warming up to rt and stirring for 2 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 (200 mL) and water (100 mL). The resulting crude material was purified by flash chromatography eluting with 95/5 CH2Cl2/MeOH yielding 850 mg (21%) of Example 203 as a white solid. 1H-NMR (CD2Cl2) δ 8.36 (s, 1H), 8.08 (d, J=1.8 Hz, 1H), 8.01 (s, 1H), 7.46–7.19 (m, 8H), 5.60 (s, 2H), 3.77 (q, J=4.4 Hz, 2H), 3.21–2.96 (m, 3H), 2.56 (m, 1H), 2.11 (m, 2H), 1.67 (m, 3H), 1.45 (t, J=4.4 Hz, 1H). LCMS RT=2.68 min; [M+H]+=456.3.

Provenance & Evidence