An easy and versatile synthesis of ureas from 2-benzylaminopyrimidine

Tetrahedron Letters

Volumn 49, Issue 50, 2008, Pages 7171-7173

  Gool, Michiel Van ^a   Bartolomé, José M ^a   Macdonald, Gregor J ^b  

^a JOHNSON AND JOHNSON   (United States)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

2 Benzylaminopyrimidine; Synthesis; Triphosgene; Ureas

Indexed keywords

2 BENZYLAMINOPYRIMIDINE; AMINE; ANILINE; PHOSGENE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; SYNTHESIS;

EID: 54549096752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.171     Document Type: Article

References (9)

1. Cherng Y.J. Tetrahedron 58 (2002) 887-890
2. Reaction of 1 with ethyl and phenyl isocyanate (1 or 5 equiv of isocyanate) was tested using dichloromethane, tetrahydrofuran and toluene as solvents at temperatures ranging from room temperature to 110 °C. Addition of a base to the reaction media (diisopropylethylamine) was also investigated. Under all the reactions conditions tried no satisfactory amounts of desired products 3a or 3j respectively were obtained.
3. Keizer H.M., Sijbesma R.P., and Meijer E.W. Eur. J. Org. Chem. 12 (2004) 2553-2555
4. Compound 1 was reacted with CDI at temperatures ranging from room temperature to 65 °C followed by addition of ethylamine and aniline and further reaction at temperatures ranging between room temperature and 50 °C in either chloroform or tetrahydrofuran as solvents.
5. Marley H., Wright S.H.B.J., and Preston P. Chem. Soc., Perkin Trans. I 10 (1989) 1727-1733
6. 3) was used.
7. Tetrahydrofuran and acetonitrile were also investigated as solvents, furnishing similar results.
8. 3CN (3j,k) or MeOH (3l).
9. 3) δ 3.38 (m, 8H) 5.10 (s, 2H) 6.73 (t, J = 4.87 Hz, 1H) 7.20-7.35 (m, 3H) 7.43 (d, J = 7.26 Hz, 2H) 8.42 (d, J = 4.77 Hz, 2H)