O.[C:2]([OH:12])(=[O:11])[C:3]1[NH:10][C:8](=[O:9])[NH:7][C:5](=[O:6])[CH:4]=1.N12CCCN=C1CCC[CH2:15][CH2:14]2.C(I)C.O>CN(C)C=O>[C:2]([O:12][CH2:14][CH3:15])(=[O:11])[C:3]1[NH:10][C:8](=[O:9])[NH:7][C:5](=[O:6])[CH:4]=1
Orotic acid monohydrate (53.19 g, 0.306 mmol) was added to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (46.51 g, 0.306 mmol) in dimethylformamide (85 ml). After stirring for 5 min., ethyl iodide (57.14 g, 0.366 mmol) was added to the solution and the mixture was heated at 60° C. for 5 hrs. Water (1 L) was added, and the resulting precipitate was collected by filtration, washed with water, and dried to give ethyl orotate (49.25 g, 88%).
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