Diphenylacetic Acid → 5-Diphenylacetyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 1884552Notes

Reaction equation

[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[C:12]1([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](O)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.ClC(Cl)C(C1C(=O)N(C)C(=O)N(C)C1=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:22]1([CH:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:19]([CH:8]2[C:9](=[O:10])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6]2=[O:7])=[O:20])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (5.00 g, 32.05 mmol), diphenylacetic acid (10.19 g, 48.03 mmol), 4-dimethylaminopyridine (1.95 g, 16.01 mmol) in dry CH2Cl2 (30 ml) was cooled to 0° C. and 1,3-dicyclohexylcarbodiimide (7:26 g, 35.22 mmol) added. The reaction mixture was stirred at room temperature overnight and filtered. The solid was washed with CH2Cl2 (150 ml) and the combined solution was washed with 2 N HCl solution (40 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallized from EtOH giving 5-diphenylacetyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 9 (6.70 g, 59%).

Workup

filtrationfiltered
washThe solid was washed with CH2Cl2 (150 ml)
washthe combined solution was washed with 2 N HCl solution (40 ml)
dry with materialThe organic phase was dried over MgSO4
customevaporated
customThe residue was crystallized from EtOH

Sources & evidence

ORD record: ord-3404e381cc1e43ccb84f34b23c99709c
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06765089B1

Reaction notes

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