Aluminium lithium hydride → HCID 178484830, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of LiAlH4 (160 mg, 2.1 mmol, 5.0 eq) in THF (5 mL) was added a solution of tert-butyl trans-4-(5,6-dimethylthieno[2,3-d]pyrimidin-4-ylamino)cyclohexylcarbamate (160 mg, 0.42 mmol, 1.0 eq) in THF (5 mL). The mixture was stirred at 80° C. for 2 hours. The reaction was quenched with a mixture of THF/H2O and filtered. The cake was washed with CH2Cl2. The filtrate was concentrated and the residue was purified by column chromatography (CH2Cl2/MeOH/Et3N=20:1:0.5) on silica gel to give desired product compound 1-44 as a white solid (72 mg, 60%). NMR (400 MHz, CDCl3) δ 1.18-1.25 (m, 4H), 1.47 (br s, 2H), 1.95-1.98 (m, 2H), 2.16-2.18 (m, 2H), 2.34 (s, 3H), 2.38 (s, 3H), 2.39 (s, 3H), 4.02-4.08 (m, 1H), 5.23 (m, 1H), 8.23 (s, 1H). MS: m/z 291.2 (M+H)+.

Provenance & Evidence