Coupling of 6-chloropurines with organocuprates derived from Grignard reagents: A convenient route to sec and tert 6-alkylpurines

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1285-1288

  Dvořáková, Hana ^a   Dvořák, Dalimil ^b   Holý, Antonín ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

PURINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0037723421     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02375-5     Document Type: Article

References (30)

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23. Similar results were obtained with 9-benzyl-6-chloropurine.
24. 2), 1.58 (m, 2H, THP), 1.76 (m, 1H, THP), 1.95 (m, 2H, THP), 2.33 (m, 1H, THP), 3.71 (m, 1H, H-5′), 4.05 (m, 1H, H-5′), 5.77 (dd, J=2.2 and 11.0Hz, H-1′), 8.71 (s, 1H, H-Pur), 8.84 (s, 1H, H-Pur).
25. CuCN was reported to give results superior to other Cu(I) salts in the coupling of tert butylmagnesium chloride with dichlorophenantroline derivatives (ref.7b).
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28. Such an addition of organolithium and organomagnesium reagents (but not organocuprates) to the 8-position of 6-chloro-9-methylpurine was reported. See, ref.8 and Tanji, K.-i.; Higashino, T. Heterocycles 1990, 30, 435. For addition of Grignard reagents to 2-oxopurinium salts see: Andresen, G.; Gundersen, L.-L.; Lundmark, M., Rise, F.; Sundell, S. Tetrahedron 1995, 51, 3655.
29. 3-MeOH, 85:15). The yields were 70-80%.
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