Dihydrouracil → ethyl 2-(2,6-dioxo-1-propyl-2,3-dihydro-1H-purin-7(6H)-yl)acetate

HRID 1696067Notes

Reaction equation

HRID 1696067 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=O)[NH:3][C:2]1=O.[CH2:9]([NH:12][C:13]([NH2:15])=[O:14])[CH2:10][CH3:11].[C:16]([CH2:18][C:19]([O:21]CC)=O)#[N:17].BrBr.[NH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(OC(OCC)OCC)C>>[NH:1]1[CH:6]=[C:5]2[C:4]([N:12]=[CH:13][NH:15]2)=[N:3][CH2:2]1.[O:14]=[C:13]1[NH:17][C:16]2[N:1]=[CH:2][N:26]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:18]=2[C:19](=[O:21])[N:12]1[CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 6

HCID 649DihydrouracilHCID 7764Ethyl cyanoacetateHCID 12176Glycine ethyl esterHCID 12303PropylureaHCID 24408BromineHCID 31214Ethyl orthoformate

Product 2

HCID 57732989ethyl 2-(2,6-dioxo-1-propyl-2,3-dihydro-1H-purin-7(6H)-yl)acetateHCID 178419787HCID 178419787, compound

Procedure

Dihydropyrimidine-dione 2 can be prepared by reacting 1-propylurea (1) and ethyl 2-cyanoacetate, which can be subsequently treated with bromine, ethyl 2-aminoacetate, and triethoxymethane to yield compound 6, ethyl 2-(2,6-dioxo-1-propyl-2,3-dihydro-1H-purin-7(6H)-yl)acetate. The obtained dihydropurine 6 can be transformed to compound 10 through methylation, hydrolysis, and a coupling reaction under CDI.

Sources & evidence

ORD record
ord-330a918d8fb148d292e5b34b3eda701b
Source dataset
uspto-grants-2012_04
Patent number
US08163761B2

Reaction notes

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