Aluminium lithium hydride → HCID 58169370, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(3-hydroxyprop-1-ynyl) pyrimidin-2-yl)thiophene-2-sulfonamide (250 mg, 0.53 mmol, 1.0 eq) in dry THF (2 mL) was added dropwise over 10 min to a mixture of LiAlH4 (250 mg, 6.58 mmol, 12.4 eq) in THF (20 mL) under nitrogen. The reaction mixture was maintained 0° C. during the addition. The reaction mixture was heated to reflux for 10 min. Then the reaction mixture was cooled to 0° C., while vigorous stirring was maintained, carefully treated with Na2SO4.10H2O (10 g) in portion and then stirred at room temperature for 10 min. The reaction mixture was filtered. The filtrate was concentrated and purified by silica gel chromatography (EtOAc/MeOH/THF from 10:0:0 to 20:1:2) to afford (E)-N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(3-hydroxyprop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 218) (100 mg, 40.0%). LC-MS (m/z)=475 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74-0.75 (m, 2H), 0.96-0.97 (m, 2H), 1.20 (s, 9H), 1.90-1.95 (m, 1H), 4.16 (m, 2H), 4.85 (s, 1H), 6.38 (d, J=16.0 Hz, 1H), 6.46 (s, 1H), 6.89 (d, J=15.2 Hz, 1H), 7.59 (d, J=3.6 Hz, 1H), 7.73 (d, J=4.0 Hz, 1H), 7.87 (bs, 1H), 8.42 (s, 1H), 9.26 (bs, 1H), 12.18 (bs, 1H).

Provenance & Evidence