B.C1COCC1.[C:7]([C:10]1[S:11][C:12]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:13][C:14]=1[NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)=[O:17])(=O)[NH2:8].Cl>C1COCC1>[NH2:8][CH2:7][C:10]1[S:11][C:12]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:13][C:14]=1[NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)=[O:17]To a solution of BH3THF (1.8 mL, 1M in THF) was added a solution of N-(2-carbamoyl-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea in THF (3 mL) and the resulting mixture was heated under reflux for 48 h. After cooling to room temp., a concentrated hydrochloric acid solution was added, and the resulting mixture was extracted with EtOAc. The organic layer was washed with a saturated Na2CO3 solution, and a saturated NaCl solution, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 0.1% NH4OH/10% MeOH/CH2Cl2 to afford N-(2-aminomethyl-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.18 g, 85%): 1H NMR (CDCl3) δ1.38 (s, 9H), 2.34 (s, 3H), 3.81 (s, 2H), 6.72 (s, 1H), 7.29 (d, J=8.6 Hz, 2H), 7.16 (d, J=8.5 Hz, 2H), 7.87 (s, 1 h); FAB-LRMS m/z 318 (M+H).
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