Ethyl Acetate → HCID 69643731, compound

Participants

Reaction Steps

The title compound was prepared from 3,4,5-trimethoxyphenylguanidinium nitrate (576 mg, 2.0 mmol), 1-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-2-cyano-3-dimethylaminopropen-1-one (660 mg, 1.8 mmol) and powdered sodium hydroxide (89 mg, 2.2 mmol) following the method described for the compound of Example 8. This gave the intermediate 4-[4-(1-tert-butoxycabonylamino-1methylethyl)phenyl]-5-cyano-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine as a yellow solid (769 mg) after column chromatography (silica, 40% ethyl acetate in hexane). This compound was treated with TFA acid in CH2Cl2 as descibed for the analogous compound of Example 8 to give the title compound as a pale yellow solid (597 mg) m.p. 167-168°. δH (d6 DMSO) 10.34 (1H, bs), 8.90 (1H, s), 7.96 (2H, bd, J 7.8 Hz), 7.73 (2H, d, J 8.2 Hz), 7.24 (2H, bs), 3.76 (6H, s), 3.63 (3H, s), 3.18 (2H, bs), 1.42 (6H, s). MS (ESI) 442 (MNa+, 16%), 420 (MH+, 57%), 403 (100%).

Provenance & Evidence