Reaction #631973

ord-775c5a2f0bcd4592b11bc1dcccc0a6d1

Reaction equation

CC(C)=O
acetone
Cc1cc(=O)nc(N)[nH]1
6-methylisocytosine
O=C(n1ccnc1)n1ccnc1
carbonyldiimidazole
→
Cc1cc(=O)nc(NC(=O)n2ccnc2)[nH]1
desired product
Cc1cc(=O)nc(NC(=O)n2ccnc2)[nH]1
N-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)-1H-imidazole-1-carboxamide

Reactants

CC(C)=O
acetone
Cc1cc(=O)nc(N)[nH]1
6-methylisocytosine
O=C(n1ccnc1)n1ccnc1
carbonyldiimidazole

Reagents

None

Solvents

CS(C)=O
dimethylsulfoxide

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture was cooled to about room temperature

Procedure

A mixture of 6-methylisocytosine (1 eq.) and carbonyldiimidazole (1.5 eq.) were combined in dimethylsulfoxide (DMSO) and the solution was stirred at 60° C. for 2 hours. The mixture was cooled to about room temperature and acetone added after which the desired product precipitated as a white powder that was collected by filtration. The procedure of A. T. Cate, P. Y. W. Dankers, H. Kooijman, A. L. Spek, R. P. Sijbesma, and E. W. Meijer, J. of Am. Chem. Soc., 2003, 125, 6860 was followed for this step. The product can be used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07935131B2uspto-grants-2011_05