Isobutylamine → HCID 59468556, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL Personal Chemistry™ microwave vial was charged with 1-{3-[4-(4-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino]-phenyl}-ethanol (149.3 mg, 0.40 mmol, prepared according to Method 22), isobutylamine (120 uL, 1.20 mmol), molybdenum hexacarbonyl (109.2 mg, 0.41 mmol), THF (2 mL), 20 mg (0.02 mmol) of Hermann's Palladacycle [trans-di-mu-acetatobis[2-9di-O-tolylphosphino)benzyl]dipalladium(II)], and DBU (180 uL, 1.20 mmol). The reaction mixture was heated to 150° C. in a microwave reactor for 15 min. The crude reaction mixture was diluted with DMSO (2 mL), filtered through a plug of silica gel, then purified by mass-triggered reverse-phase HPLC, (C-18; eluting with a 5-95% gradient consisting of 0.1% formic acid in water: 0.1% formic acid in ACN). Lyophilization of the purified fraction provided 39.5 mg (25% yield) of 5-{2-[3-(1-Hydroxy-ethyl)-phenylamino]-pyrimidin-4-yl}-thiophene-3-carboxylic acid isobutyl-amide as a white powder. 1H NMR (d6-DMSO) δ 9.49 (br. s, 1H), 8.34 (d, J=5.0 Hz, 1H), 8.20 (t, J=6.0 Hz, 1H), 8.16 (dd, J=6.0, 0.5 Hz, 1H), 7.67 (br.s, 1H), 7.49 (dd, J=5.0, 1.2 Hz, 1H), 7.15 (d, J=5.0 Hz, 1H), 7.09 (t, J=7.5 Hz, 1H), 6.80 (d, J=7.5 Hz, 1H), 4.97 (br.d, J=3.5 Hz, 1H), 4.55 (qrt, J=5.5 Hz, 1H), 2.91 (t, J=6.5 Hz, 2H), 1.67 (m, 1H), 1.19 (d, J=6.0 Hz, 3H), 0.74 (d, J=7.0 Hz, 6H); HPLC/MS m/z: 397 [MH]+.

Provenance & Evidence