Patent ID: 6617282
Filing Date: 2003-09-09
Classification: A01N,C07D

Abstract:
A process for producing 3-phenyl-2,4(1H,3H)-pyrimidinediones having the general formula (I) and their salts whereinA1 is hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cyloalkynyl, cycloalkylalkyl, each being optionally substituted, A2 is hydrogen, â€”Q1â€”A3 wherein Q1 is O, S, SO, or SO2; A3 is hydrogen or A4 (A4 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cyloalkynyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclicalkyl, each being optionally substituted), â€”Q1â€”CQ2â€”A3 wherein Q2 is O or S, â€”Q1â€”CQ2â€”Q2â€”A3, â€”Q1â€”CQ2â€”N(A3)2, â€”CQ2â€”A3, â€”CQ2â€”Q2â€”A3, â€”CQ2â€”N(A3)2, â€”N(A3)2, â€”N(Q1â€”A3)2, â€”N(CQ2â€”A3)2, â€”N(Q1â€”A3)(CQ2â€”A3), â€”N(CQ2â€”Q2â€”A3)2, â€”N(A3)â€”CQ2â€”N(A3)2, or â€”SO2â€”N(A3)2, each A3 group of (A3)2 being independently same or different, any two of (A1)l and (A2)m groups being optionally combined through a saturated or unsaturated carbon, â€”CQ2â€”, and/or hetero O, N, S, SO, or SO2 linkage to form a cyclic ring having up to 12 membered ring, each being optionally substituted,l is an integer of 1 to 5, m is an integer of 1 to 3, l+m is an integer of 2 to 5, R1 is A4, â€”Q1â€”A3, â€”Q1â€”CQ2â€”A3, â€”Q1â€”CQ2â€”Q2â€”A3, â€”Q1â€”CQ2â€”N(A3)2, â€”CQ2â€”A3, â€”CQ2â€”Q2â€”A3, â€”CQ2â€”N(A3)2, â€”N(A3)2, â€”N(Q1â€”A3)2, â€”N(CQ2â€”A3)2, â€”N(Q1â€”A3)(CQ2â€”A3), â€”N(CQ2â€”Q2â€”A3)2, â€”N(A3)â€”CQ2â€”N(A3)2, or â€”SO2â€”N(A3)2, each A3 group of (A3)2 being independently same or different, R2 is hydrogen or R1, R1 and R2 groups being optionally combined together with N of N(R1)(R2) through a saturated or unsaturated carbon, â€”CQ2â€”, and/or hetero O, N, S, SO, or SO2 linkage to form a cyclic ring having up to 12 membered ring, each being optionally substituted, which comprises reacting an isocyanate represented by the general formula (II) wherein A1, A2, l and m are as defined above, and a substituted hydrazono ester represented by the general formula (III) wherein R5 is A4, R1 and R2 are as defined above, with the presence of a Grignard reagent.