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16.17.3.4.5.3 Method 3: From Sulfanylpurines

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (2004161071.

(Methylsulfanyl)purines are good starting materials for the preparation of aminopurines. This method can be successfully employed for the synthesis of purin-6-amines, e.g. 239 (Scheme 135), from 6-(methylsulfanyl)purines, but presents some difficulties when the methylsulfanyl group is in the 2-position. Thus, the 2-(methylsulfanyl) group of 2-(methylsulfanyl)adenine could not be replaced successfully by ammonia under a variety of conditions and this experience was duplicated using alkylamines.[‌541‌] However, in the case of 2-(methylsulfanyl)purin-6-ol it is possible to perform the displacement reaction in an alcoholic amine solution (Me2NH, MeOH, 140°C, 24h) to give 2-(methylamino)purin-6-ol in 61% yield.[‌623‌]

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