2-Propenoic acid, 3-(4-formylphenyl)- → 5,6-Diamino-1-methyl-3-propylpyrimidine-2,4(1H,3H)-dione

HRID 2051168Notes

Reaction equation

HRID 2051168 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][CH2:11][CH3:12])[C:4](=[O:13])[C:3]=1[N:14]=O.[NH4+]=S.[CH:18]([C:20]1[CH:30]=[CH:29][C:23]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:22][CH:21]=1)=O>>[NH2:14][C:3]1[C:4](=[O:13])[N:5]([CH2:10][CH2:11][CH3:12])[C:6](=[O:9])[N:7]([CH3:8])[C:2]=1[NH2:1].[CH3:8][N:7]1[C:2]2[NH:1][C:18]([C:20]3[CH:30]=[CH:29][C:23](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:22][CH:21]=3)=[N:14][C:3]=2[C:4](=[O:13])[N:5]([CH2:10][CH2:11][CH3:12])[C:6]1=[O:9]

Participants

4

Reactant 2

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 108461962,4(1H,3H)-Pyrimidinedione, 6-amino-1-methyl-5-nitroso-3-propyl-

Product 2

HCID 106318125,6-Diamino-1-methyl-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 178456489HCID 178456489, compound

Procedure

5,6-Diamino-1-methyl-3-propyl-2,4(1H,3H)pyrimidinedione was prepared freshly from 6-amino-1-methyl-5-nitroso-3-propyl-2,4-(1H,3H)pyrimidinedione by ammonium sulfide reduction using the method of V. Papesch, M. Grove, and E. F. Schroeder (U.S. Pat. No. 2,602,795). This diamine (2.00 g, 10.0 mmol) was condensed with 4-formylcinnamic acid (1.76 g, 10.0 mmol) by the procedure of Example 2 to give the title compound as an ivory powder, after crystallization from N,N-dimethylformamide-water; mp>300° C. Analysis for (C18H18N4O4.1/5 DMF): C,60.54; H,5.30; N,15.94. Found: C,60.52; H,5.22; N,16.03.

Sources & evidence

ORD record
ord-03b91ba3b99a48cc808b5a6baa2f6d4a
Source dataset
uspto-grants-1991_05
Patent number
US05017577

Reaction notes

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