Synthesis of 6-ethynylpurine derivatives

Tetrahedron Letters

Volumn 49, Issue 23, 2008, Pages 3782-3784

  Nagy, András ^a   Kotschy, András ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1 ETHYNYLCYCLOHEXANOL; 2 METHYLBUT 3 YN 2 OL; 6 ETHYNYLPURINE DERIVATIVE; 6 HALOPURINE DERIVATIVE; ACETYLENE; BUTANOL; CYCLOHEXANOL DERIVATIVE; PURINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; REACTION ANALYSIS; SONOGASHIRA REACTION;

EID: 43049114884     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.011     Document Type: Article

References (19)

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14. 2 and 54 mg (0.285 mmol, 2 mol %) of CuI was stirred in 20 ml of THF at ambient temperature, under an argon atmosphere. After 1 min, 16 mmol of 2-methyl-3-butyn-2-ol or 1-ethynyl-cyclohexanol and 5.0 ml (35.5 mmol) of triethylamine were added to the mixture. Stirring was continued until the starting material was consumed (ca. 16 h) and then the resulting thick suspension was filtered. The precipitate was washed with water and cold ethyl acetate and dried in vacuum to yield the appropriate compound (3b or 3c) as a white solid.
15. The coupling reactions of 2-amino-6-iodopurine with 2a and 2b were also successful but we were unable to remove the organic end-groups (acetone or cyclohexanone) from the resulting compounds without significant decomposition.
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19. 5O: C, 70.97; H, 4.82; N, 19.71%. Found: C, 70.56; H, 4.93; N, 19.50%.