Potassium Carbonate → 5-Acetyl-1-benzyl-3-(4-fluorobenzyl)-2,4(1H,3H)-pyrimidinedione

HRID 2099243Notes

Reaction equation

HRID 2099243 reaction equation
[C:1]([C:4]1[C:5](=[O:18])[NH:6][C:7](=[O:17])[N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1)(=[O:3])[CH3:2].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:6]2[C:5](=[O:18])[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][N:8]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]2=[O:17])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 3334243HCID 3334243, compound

Product 1

HCID 38140685-Acetyl-1-benzyl-3-(4-fluorobenzyl)-2,4(1H,3H)-pyrimidinedioneYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in 93.7% yield by benzylation of 5-acetyl-1-benzyluracil (2e) with 2 equiv of 4-fluorobenzyl bromide and 2 equiv of potassium carbonate in DMF. Mp. 106-108° C. 1HNMR (CDCl3): 8.23 (s, 1H), 7.30-7.50 (m, 7H), 7.00 (m, 2H), 5.12 (s, 2H), 5.01 (s, 2H), 2.61 (s, 3H). 13CNMR (CDCl3): 194.3, 162.4 (d, J=246.4 Hz), 160.7, 151.0, 148.4, 134.4, 132.1 (d, J=3.4 Hz), 131.1 (d, J=8.2 Hz), 129.2, 128.9, 128.2, 115.3 (d, J=21.6 Hz), 112.3, 53.4, 44.2, 30.6. FAB-HRMS: [M+H]+ Calcd. for C20H18FN2O3 353.1301. Found 353.1310.

Sources & evidence

ORD record
ord-5c202ffc0d064558919a822674c30fce
Source dataset
uspto-grants-2009_08
Patent number
US07569573B2

Reaction notes

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