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7‐Deazapurines II. Syntheses and reactions of 5‐aminopyrrolo[2,3‐ d ] pyrimidine‐6‐carbonitrile and related compounds
Author(s) -
Kim Dong Han,
Santilli Arthur A.
Publication year - 1971
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570080505
Subject(s) - chemistry , pyrimidine , ring (chemistry) , pyridine , formamide , carbon disulfide , medicinal chemistry , disulfide bond , stereochemistry , organic chemistry , biochemistry
The reaction of 4‐chloro‐2‐phenyl‐5‐pyrimidinecarbonitrile (III) with N ‐methylglycinonitrile gave 4‐[(eyanomethyl)methylamino]‐2‐phenyl‐5‐pyrimidinecarbonitrile (VIa), which upon cycli‐zation under Dieckmann conditions afforded 5‐amino‐7‐methyl‐2‐phenyl‐7 H ‐pyrrolo[2,3‐ d ]‐pyrimidine‐6‐carbonitrile (VIIa). Other examples (VIIb and VIIc) were prepared similarly from the reactions of III with glycinamide and ethyl glycinate, respectively. The preparation of simple 5‐amino derivatives of the pyrrolo[2,3‐ d ] pyrimidines thus synthesized is described. The alkyla‐tion of VIIc with N ‐cyeloheptylchloroacetamide took place at the ring nitrogen, giving XII. The reaction of VIIa with formamide gave 4‐amino‐5‐methyl‐7‐phenyl‐5 H ‐pyrrolo[2,3‐ d :4,5‐ d ′ ]‐dipyrimidine (XIII), the first member of a new ring system. Treatment of VIIa with carbon disulfide and pyridine afforded another example of this new ring system, 1,5‐dihydro‐5‐methyl‐7‐phenyl‐2 H ‐pyrrolo[2,3‐ d :4,5‐ d′ ] dipyrimidine‐2,4‐(3 H )dithione (XIV).