Morpholine → HCID 71272706, compound

Participants

Reaction Steps

To the solution of 5,7-dichloro-2-methyl-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine (0.05 g, 0.146 mmol) in 1,4-Dioxane (5 mL) was added ammonium hydroxide (0.508 mL, 3.65 mmol). The reaction was stirred at rt for 3 days. The reaction was concentrated to give the solid. To the mixture of the solid in Ethanol (1 mL) was added morpholine (0.382 mL, 4.38 mmol). The mixture was subjected to MW irradiation at 150° C. for 6 h. The reaction mixture was concentrated. The crude was purified by reversed phase HPLC (20˜50% CH3CN (0.1% TFA)/Water (0.1% TFA)). The fractions from purification were concentrated. NaHCO3 solution (3 mL) was added in and extracted with EtOAc (20 mL). The organic phase was washed with Brine (5 mL), dried (MgSO4) and concentrated to give the product as solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.18 (s, 3H) 3.46-3.52 (t, J=5.24 Hz, 4H) 3.65-3.74 (t, J=4.52 Hz, 3H) 4.28 (s, 2H) 5.49 (s, 1H) 7.07 (br. s., 2H) 7.31 (m, 1H) 7.37-7.43 (m, 1H) 7.45-7.52 (m, 2H) 7.75 (d, J=8.34 Hz, 1H) 7.85-7.93 (m, 1H) 8.54 (m, 1H); LC/MS: MS (ES+) m/e 374.0 [M+H]+.

Provenance & Evidence