Cesium carbonate → 3-(4-Chlorophenyl)-2-(2-chlorophenyl)-7-(2,2,2-trifluoroethoxy)-pyrazolo[1,5-a]pyrimidine

Temperatur

60 °C

To a mixture of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidin-7-ol (I-12A-1a; 65 mg, 0.18 mmol) and Cs2CO3 (59 mg, 0.18 mmol) in DMF (1.5 ml) was added a DMF solution (0.1 ml) of trifluoromethanesulfonic acid 2,2,2-trifluoroethyl ester (42 mg, 0.18 mmol). After stirring at 60° C. overnight, the mixture was extracted from pH 7 water with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and then concentrated, in vacuo, to afford the crude product. Purification on a Chromatotron using 1:0:0, 20:1:0, and then 20:0:1 methylene chloride/ethyl acetate/methanol as eluants afforded, in addition to two N-alkylated isomers, product 12A-1 (16.5 mg, 21%) as a solid: +ESI MS (M+1) 438.4; 1H NMR (400 MHz, CD3OD) δ 8.56 (d, J=5.0 Hz, 1H), 7.55–7.41 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 6.80 (d, J=5.0 Hz, 1H), 5.16 (q, J=7.9 Hz, 2H).

1. extractionthe mixture was extracted from pH 7 water with ethyl acetate
2. washThe combined organic layers were washed with brine
3. dry with materialdried (MgSO4)
4. concentrationconcentrated, in vacuo
5. customto afford the crude product
6. customPurification on a Chromatotron
7. custom20:0:1 methylene chloride/ethyl acetate/methanol as eluants afforded, in addition to two N-alkylated isomers, product 12A-1 (16.5 mg, 21%) as a solid

ORD-Eintrag

ord-47cd86927e724e949d798577766f0848

Quelldatensatz

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07176210B2