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Seela, F.; Ramzaeva, N.; Rosemeyer, H., Science of Synthesis, (2004) 16, 973.
Diethoxymethyl acetate remains the best reagent for the preparation of 8-unsubstituted purines, with only a few side reactions being encountered.[207–211] Treatment of commercially available 4,6-dichloropyrimidin-5-amine with 2–3 equivalents of (15N)ammonia in ethanol and diisopropylamine (200°C, ∼7 atm, 12 h) gives the monosubstituted product 4-chloropyrimidine-5,6[15N]-diamine (95% yield). The annulation reaction is performed in neat diethoxymethyl acetate (100°C, 3.5 h) to give 6-chloro[9-15N]purine 36 (Scheme 29).[211]
Meeeee 88 8-Meeeee[8-88M]eeeeee ee Meeeeeeeeee ee 8-Meeeeeeeeeeeeeee-8,8[88M]eeeeeee[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8M-[8-88M]eeeeee (88):[888]
Me eeeeeeeeeeeeee eeeeeee (88 eM) ee e eeeeeeee eeeee eee eeeee 8-eeeeeeeeeeeeeeee-8,8[88M]-eeeeeee (8.8 e, 8.88 eeee), eee eee eeeeeee eee eeeeeeeeee ee 888°M eee 8.8 e. Meeeeeeee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee. Meeeeee eeee MeMMe eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM) eeee e eeeee eeeeee; eeeee: 8.88 e (88%); ee >888°M (eee).
References
[207] | Meeeee, M.; Meeeeeeee, M.; Meeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
[208] | Meeeeeeeee, M. M.; Meeeee, M., Me., M. Me. Meee. Mee., (8888) 88, 8888. |
[209] | Meeeeee, M. M.; Meeeee, M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 888. |
[210] | Mee, M. M.; eee Meeee, M., M. Mee. Meee., (8888) 88, 888. |
[211] | Meee, M. M.; Meeee, M.; Meeeeee, M. M.; Meeee, M. M., MMM, M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e8, 888.