Aluminium lithium hydride → HCID 178484829, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl trans-4-(6,6-dimethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-ylamino)cyclohexanylcarbamate (210 mg, 0.49 mmol) in 10 mL of THF was added LiAlH4 (88 mg, 2.44 mmol, 5.0 eq) carefully at 0° C. The resulting mixture was heated at reflux for 2 h and cooled down. The reaction was cooled to 0° C. and quenched with a mixture of THF/H2O. Extracted with EtOAc (3×20 mL) and the combined organics were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by column chromatography in silica gel (DCM/MeOH/NH4OH=100:8:1) to give the product as white solid (140 mg, 80%). 1H NMR (400 MHz, CDCl3) δ1.01 (s, 6H), 1.18-1.30 (m, 4H), 1.58 (t, J=6.4 Hz, 2H), 1.96 (br s, 1H), 1.98-2.01 (m, 2H), 2.17-2.19 (m, 2H), 2.38-2.40 (m, 1H), 2.41 (s, 3H), 2.56 (s, 2H), 2.73-2.76 (m, 2H), 4.07-4.10 (m, 1H), 5.01 (d, J=7.2 Hz, 1H), 8.29 (s, 1H). MS: m/z 345.1 (M+H).

Provenance & Evidence