Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction

Tetrahedron Letters

Volumn 51, Issue 22, 2010, Pages 2948-2950

  Fletcher, Steven ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 CHLOROPURINE; 6 N CYCLOPENTYLADENOSINE; ADENINE; ADENOSINE; ADENOSINE A1 RECEPTOR AGONIST; NITROGEN; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DEPROTECTION REACTION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MITSUNOBU REACTION; REACTION TIME; SUBSTITUTION REACTION;

EID: 77951258349     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.103     Document Type: Article

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19. 2), 7.15-7.20 (m, 6H, Tr), 7.28-7.34 (m, 9H, Tr), 7.98 (s, 1H, H8), 8.45 (s, 1H, H2); LRMS (ESI) m/z 533.9 (M+H).
20. 9-NH); LRMS (ESI) m/z 192.3 (M+H).
21. 2/Hex/EtOAc, 3:6:1. Intermediate purines 7d, 7f and 7h could not be completely purified by this method, being contaminated with varying amounts of DIAD-related by-products. Nevertheless, complete purification of the target purines 8d, 8f and 8h was achieved after Boc and Tr removal in the overall yields shown (two steps) in Table 1.
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24. 2 (cyclopentyl)), 4.60 (dd, J = 11, 6 Hz, 1H, H2′), 5.17 (d, J = 5 Hz, 1H, OH), 5.39-5.44 (m, 2H, 2 OH), 5.88 (d, J = 6 Hz, 1H, H1′), 7.76 (br m, 1H, NH), 8.19 (s, 1H, H8), 8.34 (s, 1H, H2); LRMS (ESI) m/z 336.2 (M+H).