Methanol → HCID 66779989, compound

Participants

Reaction Steps

A mixture of 4-[(3-chloro-2-methylphenyl)methyl]-5-(methylthio)-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (500 mg, 1.182 mmol) and sodium perborate tetrahydrate (700 mg, 3.85 mmol) in Methanol (5 mL) was irradiated in a microwave reactor at 110° C. for 15 min. The reaction was repeated three additional times. The four reaction mixtures were poured into brine and extracted with CH2Cl2 (4×). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was purified on silica gel (ISCO, 0-7% MeOH in CH2Cl2), but separation failed. The fractions containing product were combined, absorbed onto silica gel and resubmitted for purification on silica gel (ISCO, 0-5% MeOH in CH2Cl2), but again no separation was observed. The residues from the combined fractions were finally purified using Chiralpak IA (101×210 mm, 100% CH3OH, 500 ml/min) to give 4-[(3-chloro-2-methylphenyl)methyl]-5-(methyloxy)-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (820 mg, 1.995 mmol, 42.2% yield) as a white powder. LC/MS (ES+): [M+H]+=407.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.36 (d, J=7.83 Hz, 1H), 7.15 (t, J=7.83 Hz, 1H), 6.72 (d, J=7.58 Hz, 1H), 5.34 (s, 2H), 3.85 (s, 3H), 3.60-3.74 (m, 4H), 3.51 (t, J=4.67 Hz, 4H), 2.41 (s, 3H).

Provenance & Evidence