tert-Butanol → HCID 59468607, compound

Participants

Reaction Steps

5-(2-m-Tolylamino-pyrimidin-4-yl)thiophene-2-carboxylic acid (200 mg, 0.643 mmol) was treated with Diphenylphosphorylazide (277 uL, 1.28 mmol) and triethylamine (180 uL, 1.28 mmol) in t-BuOH (4 mL) for 7 hours at 100° C. The reaction was cooled to room temperature, concentrated in vacuo and purified by SiO2 chromatography (0-50% B over 25 min.; Hexanes/EtOAc) to afford [5-(2-m-Tolylamino-pyrimidin-4-yl)-thiophen-2-yl]-carbamic acid tert-butyl ester (101.8 mg, 41.1%). 1H NMR (500 MHz, DMSO-d6) δ 1.49 (s, 9H), 2.32 (s, 3H), 6.57 (d, J=4 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 7.13 (t, J=8 Hz, 1H), 7.14 (d, J=5 Hz, 1H), 7.47 (br m, 1H), 7.68 (d, J=4 Hz, 1H), 7.83 (br s, 1H), 8.32 (d, J=5 Hz, 1H), 9.42 (s, 1H), 10.8 (br s, 1H). MS: m/z 383 (M+H+).

Provenance & Evidence