Hydrochloric Acid → HCID 71532471, compound

Participants

Reaction Steps

To the solution of 5,7-dichloro-2-methyl-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine (1.5 g, 4.38 mmol) in Tetrahydrofuran (THF) (40 mL) was added sodium hydroxide (21.92 mL, 43.8 mmol). The reaction was stirred at rt for 18 h and heated at 50° C. for 7 h. The reaction was concentrated and acidified. The reaction mixture was extracted with EtOAc (80 mL×2). The organic phases were combined, dried and concentrated. The mixture was transferred to a 20 mL MW vial. Morpholine (1.909 mL, 21.92 mmol) and Ethanol (2 mL) was added in. The mixture was subjected to MW irradiation at 150° C. for 3 h. Water (10 mL) was added to the reaction mixture which was acidified with 6 N HCl. The reaction was extracted with EtOAc (100 mL×3). The organic phases were combined, dried and concentrated. To the resulted solid was added POCl3 (6.13 mL, 65.7 mmol) and N,N-diethylaniline (1.308 g, 8.77 mmol). The reaction was heated at 90° C. for 5 h. The reaction was cooled down. Crushed ice was added in. The aqueous mixture was extracted with EtOAc (100 mL×3). The organic phases were combined, dried and concentrated. The crude was purified on silica column (EtOAc/Hexane: 20˜40%) to give the product (1.02 g, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.20 (s, 3H) 3.54-3.74 (m, 8H) 4.33 (s, 2H) 7.00 (s, 1H) 7.32 (d, J=6.57 Hz, 1H) 7.37-7.44 (m, 1H) 7.45-7.55 (m, 2H) 7.76 (d, J=8.08 Hz, 1H) 7.90 (m, 1H) 8.44 (m, 1H); LC/MS: MS (ES+) m/e 393.1 [M+H]+.

Provenance & Evidence