Trifluoroacetic acid → HCID 60207822, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of tert-butyl 5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-ylcarbamate from step 1 in CHCl3 (30 mL) cooled to 0° C. was injected trifluoroacetic acid (3 mL) and let stir for 23 h at 23° C. The reaction solvent was then evaporated and redissolved in CH2Cl2 and washed with saturated NaHCO3 solution. The organic layer dried (sodium sulfate) and concentrated, whereupon the residue was purified by silica gel flash column chromatography (gradient from 2% methanol in dichloromethane to 10% methanol in dichloromethane) afford 5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-amine (361 mg, 38% yield over 3 steps) as a yellow oil. 1H NMR (500 MHz, DMSO) δ 8.55 (s, 1H), 7.83 (dd, J=3.91, 0.98 Hz, 1H), 7.69 (dd, J=5.38, 0.98 Hz, 1H), 7.46 (s, 1H), 7.21 (dd, J=4.89, 3.91 Hz, 1H), 4.86 (bs, 2H), 3.19 (t, J=7.82 Hz, 2H), 2.53 (s, 3H), 4.53 (m, 2H), 1.36 (sex, J=7.83 Hz, 2H), 0.84 (t, J=7.34 Hz, 3H). LCMS (ES+) m/z 314 (M+1).

Provenance & Evidence