Hydrochloric Acid → HCID 71275064, compound

Participants

Reaction Steps

To the solution of 5,7-dichloro-2-methyl-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine (0.2 g, 0.584 mmol) in Tetrahydrofuran (THF) (5 mL) was added sodium hydroxide (2.045 mL, 4.09 mmol). The reaction was stirred at rt for 18 h. The reaction was acidified. The reaction was extracted with EtOAc (80 mL×2). The organic phases were combined, washed with Brine, dried and concentrated. The mixture was transferred to 5 mL MW vial. Morpholine (0.509 mL, 5.84 mmol) and Ethanol (1 mL) was added in. The reaction mixture was subjected to MW irradiation at 150° C. for 3 h. 6 N HCl was added to the reaction to acidify the solution. The reaction mixture was extracted with EtOAc (50 mL×2). The organic phases were combined, washed with Brine, dried and concentrated. The residue was purified by reversed phase HPLC (25˜55% CH3CN (0.1% TFA)/Water (0.1% TFA)) to give the product (30 mg, 11%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.17 (s, 3H) 3.52-3.64 (m, 8H) 3.66-3.73 (t, J=4.63 Hz, 4H) 3.74-3.82 (t, J=4.44 Hz, 4H) 4.30 (s, 2H) 5.78 (s, 1H) 7.31 (d, J=6.57 Hz, 1H) 7.37-7.43 (m, 1H) 7.43-7.53 (m, 2H) 7.75 (d, J=8.08 Hz, 1H) 7.84-7.94 (m, 1H) 8.46-8.56 (m, 1H); LC/MS: MS (ES+) m/e 444.2 [M+H]+.

Provenance & Evidence