反应详情

(1R,cis)-4-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol (from part d of this example, 9.63 g, 40.0 mmol), triethylorthoformate (150 mL), and concentrated hydrochloric acid (14 mL) were stirred for 3 hours. Volatiles were evaporated and the residual solid was partitioned between chloroform (300 mL) and saturated aqueous sodium carbonate (100 mL). The aqueous layer was extracted with chloroform (2×100 mL). The combined chloroform layers were dried (sodium sulfate). Volatiles were evaporated under reduced pressure and the residual yellow glass was chromatographed on silica gel. Elution with ethyl acetate gave title compound as white needles from ethyl acetate (7.45 g, 74%), m.p. 121–124° C.; 1H-NMR (DMSO-d6) δ 8.81 (s, 1H), 8.64 (s, 1H), 6.24 and 6.21 (two m, 2H), 5.75 (m, 1H), 4.75 (t, J=5.4 Hz, 1H), 3.34 (m, 2H), 2.95 (m, 1H), 2.75 (m, 1H), 1.75 (m, 1H).

1. customwere stirred for 3 hours
2. customVolatiles were evaporated
3. customthe residual solid was partitioned between chloroform (300 mL) and saturated aqueous sodium carbonate (100 mL)
4. extractionThe aqueous layer was extracted with chloroform (2×100 mL)
5. dry with materialThe combined chloroform layers were dried (sodium sulfate)
6. customVolatiles were evaporated under reduced pressure
7. customthe residual yellow glass was chromatographed on silica gel
8. washElution with ethyl acetate