Iodine mediated an efficient and greener thiocyanation of aminopyrimidines by a modification of the Kaufmann's reaction

Tetrahedron Letters

Volumn 52, Issue 21, 2011, Pages 2652-2654

  Rodríguez, Ricaurte ^a   Camargo, Patricia ^a   Sierra, César A ^a   Soto, Carlos Y ^a   Cobo, Justo ^b   Nogueras, Manuel ^b  

^a UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

^b UNIVERSITY OF JAÉN   (Spain)

Author keywords

2 Aminothiazolo 4,5 d pyrimidines; Aminopyrimidines; Kaufmann's reaction; Molecular iodine; Thiocyanation

Indexed keywords

2 AMINO 4,6 DICHLOROPYRIMIDIN; 2 MINOTHIAZOLO[4,5 DEXTRO]PYRIMIDINE DERIVATIVE; 2,4,6 TRIAMINOPYRIMIDINE; 5 THIOCYANATOPYRIMIDINE DERIVATIVE; BROMINE; CHLORINE; HALOGEN; IODINE; ISOTHIOCYANOPYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; REAGENT; SOLVENT; TOXIC SUBSTANCE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYST; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; ESCHERICHIA COLI; HEATING; KAUFMANN REACTION; LOW TEMPERATURE; METHODOLOGY; MOLECULAR DYNAMICS; MYCOBACTERIUM; MYCOBACTERIUM SMEGMATATIS; REACTION TIME; ROOM TEMPERATURE; SAFETY; THIOCYANATION;

EID: 79955477023     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.058     Document Type: Article

References (24)

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8. A recent search on the web (SciFinder®) showed some thiocyanates of aminopyrimidine derivatives unfortunately in most of the cases there were not bibliographic information available.
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20. General procedure for thiocyanation of aminopyrimidine derivatives: Ammonium thiocyanate (3 mmol) and iodine (1.0 mmol) are added at room temperature to a stirred solution of the corresponding aminopyrimidine derivative (1.0 mmol) in methanol (10 mL). After completion of the reaction (TLC control), a sodium thiosulfate solution [20% (w/v)] is added to destroy the remaining iodine. The solid formed is filtered off, washed with water, and recrystallized from a methanol/water solution. For more details see Table 1 and Supplementary data.
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22. At the same time the typical signal for a tertiary carbon at C-5 position disappears in DEPT-135 spectra.
23. For details see Supplementary data.
24. M.Y. Jang, S. Jonghe, K. Segers, J. Anné, and P. Herdewijn Bioorg. Med. Chem. 19 2011 702