A novel three-component one-pot pyrimidine synthesis based upon a coupling-isomerization sequence

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1967-1970

  Muller, Thomas J J ^a   Braun, Roland ^a   Ansorge, Markus ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE DERIVATIVE;

ARTICLE; BIOCHEMISTRY; METHODOLOGY; SYNTHESIS;

BIOCHEMISTRY; PYRIMIDINES;

EID: 0034729575     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006046e     Document Type: Article

References (29)

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17. For an efficient repetitive synthesis of (oligo)pyrimidines based upon vinamidinium salt amidine condensations, see: Gompper, R.; Mair, H.-J. Polborn, K. Synthesis 1997, 696
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25. The propynols 4 were synthesized according to Krause, N.; Seebach, D. Chem. Ber. 1987, 120, 1845.
26. The amidinium salts 5 were synthesized according to a modification of the Pinner reaction; see: Schaefer, F. C.; Peters, G. A. J. Org. Chem. 1961, 26, 412.
27. 3)2 and 2 mg (0.01 mmol) of CuI in a degassed mixture of 10 mL of THF and 5 mL of triethylamine under nitrogen was added a solution of 145 mg (1.05 mmol) of 1-(3-thienyl)-propyn-1-ol (4d) in 10 mL of THF dropwise at room temperature over a period of 30 min. The mixture was heated to reflux temperature for 16 h. After the mixture cooled to room temperature, 165 mg (1.00 mmol) of 2-thienyl amidinium chloride (5a) was added and the reaction mixture was heated to reflux temperature for 48 h. After cooling the solvents were removed in vacuo, and the residue was dissolved in dichloromethane and filtered through a short pad of silica gel. The solvents were evaporated in vacuo, and the residue was recrystallized from dichloromethane/pentane to give 255 mg (70%) of analytically pure 6a as a beige powder.
28. All compounds have been characterized spectroscopically and by correct elemental analysis.
29. 13C NMR Spektroskopie; Georg Thieme Verlag: Stuttgart, New York, 1984; p 351.