反应详情

A solution of (+)-(1R,cis)-4-amino-2-cyclopentene-1-methanol hydrochloride (from deblocking of 10.66 g, 50.0 mmoles of (+)-(1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate as described in part c of this example), 5-amino-4,6-dichloropyrimidine (Aldrich, 16.40 g, 0.100 mole), and triethylamine (15.2 g, 0.150 mole) in 1-butanol (25 mL) was refluxed under nitrogen for 18 hours. The solution was cooled and 1 N sodium hydroxide (100 mL) was added. Volatiles were evaporated under reduced pressure and the residual solid was chromatographed on silica gel. Title compound eluted with 5% methanol-chloroform as a pale yellow glass (10.8 g). Crystallization of such a sample from ethyl acetate gave title compound as white needles, m.p. 144–146° C.; 1H-NMR (DMSO-d6) δ 7.75 (s, 1H), 6.76 (d, J=6.8 Hz, 1H), 5.93 and 5.82 (two m, 2H), 5.11 (m, 3H), 4.66 (t, J=5.3 Hz, 1H), 3.40 (br t, J=6.1 Hz, 2H), 2.75 (m, 1H), 2.20 (m, 1H), 1.38 (m, 1H).

1. temperaturewas refluxed under nitrogen for 18 hours
2. temperatureThe solution was cooled
3. customVolatiles were evaporated under reduced pressure
4. customthe residual solid was chromatographed on silica gel
5. washTitle compound eluted with 5% methanol-chloroform as a pale yellow glass (10.8 g)
6. customCrystallization of such a sample from ethyl acetate