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ChemicalBook CAS DataBase List 6-Dimethylaminopurine
938-55-6

6-Dimethylaminopurine synthesis

9synthesis methods
6-Dimethylaminopurine synthesis: 2-Methylmercapto-4-amino-6-dimethylaminopyrimidine (VI) was smoothly nitrosated in 10% acetic acid to the 5-nitrosopyrimidine (V) in 95% yield. Reduction of V with sodium hydrosulfite to the triamine (IV), followed by formylation gave the 5-formamidopyrimidine (VII) in 76% over-all yield for the two steps. Reductive formylation of V directly to VI1 with zinc and formic acid, although more rapid, was less efficient (50% yield). Ring closure of VII to 2-methyhercapto-6-dimethylaminopurine (X) was best done on a small scale by short fusion at 250°(99% yield), although boiling quinoline, formamide, or dilute alcoholic sodium hydroxide could also be employed. The latter reagent was most efficient on a large scale. Desulfurization of X with Raney nickel (7) in 1 N sodium hydroxide at 100° afforded the final product, 6-dimethylaminopurine (XII) in 43% yield.This compound was identical in all respects with the C7H9N5 moiety from puromycin (2).
synthesis of 6-Dimethylaminopurine
-

Yield:-

Steps:

Multi-step reaction with 2 steps
1: 47 percent / POCl3, dimethylaniline / 0.5 h / Heating
2: 81 percent / ethanol / 12 h / 150 °C / high pressure

References:

LaMontagne, Maurice P.;Smith, David C.;Wu, Geng-Shuen [Journal of Heterocyclic Chemistry,1983,vol. 20,p. 295 - 299]

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