反应详情

A solution of 428 mg. of the 2-amino-6-chloro-8-azapurine of Example 8 in 25 ml. of liquid ammonia was heated for 18 hours at 60° C. in a stainless steel bomb containing a glass liner. The bomb was chilled and opened, and ammonia was evaporated with a current of nitrogen. The residual solid was triturated with water (12 ml.), collected by filtration, washed with cold water, and dried in vacuo at 56° C.: yield, 359 mg. (90%); m.p. 245°-247° C. dec. (inserted at 200° C., 3° C./min.). A second crop of the carbocyclic analog of 2,6-diamino-8-azapurine 2'-deoxyribofuranoside was isolated in the same way from the concentrated filtrate: weight 31 mg. (total yield, 98%); m.p. 244°-246° C. dec. (inserted at 200° C., 3° C./min.). A solution of the two portions in boiling water (35 ml.) was treated with a small amount of activated charcoal, concentrated to about one-half of the original volume, and refrigerated. The white crystalline compound (Formula VII, X=NH2) was separated by filtration, washed with cold water, and dried in vacuo at 56° C.: weight, 350 mg. (92% recovery); m.p. 246°-248° C. dec. (inserted at 200° C., 3° C./min.); TLC, 1 spot (40 mcg., 2:1 chloroform-methanol as developing solvent); UV max 285 nm (ε7700), 255 (ε9800), 214 (ε26,000) at pH 1; 287 (ε10,600), 258 (ε5800), 223 (ε25,800) at pH 7; 287 (ε10,700), 258 (ε5800), 223 (ε26,000) at pH 13; MS (direct-probe temperature, 220° C.), m/e 265 (M), 248 (M-OH), 235, 234 (M-CH2OH), 218 (M-OH-CH2OH+H), 206 (M-CH2OH-N2), 190 (M-75), 178 (P+C2H4), 152 (P+2H), 151 (P+H); IR (strong bands; 1800-600 cm-1 region) 1670, 1630, 1600, 1585 vs, 1480 vs, 1420, 1020, 785, 670.

1. additioncontaining a glass liner
2. temperatureThe bomb was chilled
3. customammonia was evaporated with a current of nitrogen
4. customThe residual solid was triturated with water (12 ml.)
5. filtrationcollected by filtration
6. washwashed with cold water
7. customdried in vacuo at 56° C.
8. customyield
9. customm.p. 245°-247° C. dec. (inserted at 200° C., 3° C./min.)