Subscribe to RSS
DOI: 10.1055/s-0029-1219573
N,N′-Dimethyl Urea
Publication History
Publication Date:
10 March 2010 (online)
Introduction
N,N′-Dimethyl urea (DMU) (1,3-dimethyl urea, methyl carbamide) is a colourless solid and a non-volatile, versatile and powerful reagent for the synthesis of nitrogen-containing heterocyclic compounds. It is used for the synthesis of caffeine, theophylline, pharmaceuticals, textile aids, herbicides, etc. It also finds application in metal-ion complexation, material science, etc. In 1954, Blick and Godt synthesized the important building block N,N′-dimethyl-6-amino uracil from a mixture of DMU, cyanoacetic acid, and acetic anhydride with exclusion of moisture under stirring at 60 ˚C for 3 h. [¹] It is a very important starting material for the synthesis of pyrimidine derivatives.
Scheme 1
- 1
Blicke FF.Godt HC. J. Am. Chem. Soc. 1954, 76: 2798 - 2
Grinberg FL. Prom. Org. Khim. 1939, 6: 31 - 3
Shigeru M.Makoto S.Isamu K.Akira S.Masaykki M. Hokkaido Daigaku Suisangakubu Kenkyu Iho 1978, 29: 75 - 4
Singh K.Arora D.Singh S. Tetrahedron Lett. 2006, 47: 4205 - 5
Bailey CD.Houlden CE.Bar GLJ.Lloyd-Jones GC.BooKer-Milburn KI. Chem. Commum. 2007, 2932 - 6
Willis MC.Snell RH.Fletcher AJ.Woodward RL. Org. Lett. 2006, 8: 5089 - 7
Gozalishvili LL.Beryozkina TV.Omelchenko IV.Zubatyuk RI.Shishkin OV.Kolos NN. Tetrahedron 2008, 64: 8759 - 8
Paquin L.Hamelin J.Tezier-Boullet F. Synthesis 2006, 1652 - 9
Bar GLJ.Lloyd-Jones GC.Booker-Milburn KI. J. Am. Chem. Soc. 2005, 127: 7308 - 10
Nilsson BL.Overman LE. J. Org. Chem. 2006, 71: 7706 - 11
Ripka AS.Diaz DD.Sharpless KB.Finn MG. Org. Lett. 2003, 5: 1531 - 12
Abad A.Agullo C.Cunat AC.Vilanova C. Synthesis 2005, 6: 915 - 13
Kolos NN.Gozalishvili EN.Knyazeva IV. Russ. J. Org. Chem. 2009, 45: 124