Triethylamine → 2-(3-Chlorophenyl)pyrazolo[1,5-c]pyrimidine

To a cold (0° C.) solution of 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethanone oxime (5.0 g, 20.2 mmol) in ethylene glycol dimethyl ether (50 mL) was added trifluoroacetic anhydride (2.85 ml, 20.2 mmol) dropwise). The reaction mixture was warmed to room temperature and stirred 10 minutes then recooled to 0° C. A solution of triethylamine (5.63 mL, 40.4 mmol) in ethylene glycol dimethyl ether was added and the resultant solution was stirred at room temperature 1.5 hours. Iron (II) chloride (25 mg, 0.20 mmol) was added and the reaction mixture was refluxed 3 hours. The reaction mixture was cooled to room temperature and the excess ethylene glycol dimethyl ether was removed in vacuo. The resultant oil was chromatographed (9:1 to 4:1 hexanes:ethyl acetate) to provide 2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidine (3.2 g, 69%) as a pale yellow solid. Rf 0.27 (4:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 9.25 (s, 1H), 8.00 (s, 1H), 7.88–7.81 (m, 2H), 7.46–7.39 (m, 3H), 6.81 (s, 1H); MS m/z 230 (M+1).

1. customthen recooled to 0° C
2. temperaturethe reaction mixture was refluxed 3 hours
3. temperatureThe reaction mixture was cooled to room temperature
4. customthe excess ethylene glycol dimethyl ether was removed in vacuo
5. customThe resultant oil was chromatographed (9:1 to 4:1 hexanes:ethyl acetate)

ORD record

ord-ff95e61d83914af5aeae385f9da97768

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07247626B2