Pyrimidine → HCID 178516499, compound

HRID 582903Notes

Reaction equation

HRID 582903 reaction equation
N1C=CC=NC=1.[C:7]([OH:10])(=O)[CH3:8].C(N)=N.[C:14]([C:22]1[N:27]=CC=[CH:24][N:23]=1)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[OH:10][C:7]1[CH:8]=[CH:24][N:23]=[C:22]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:27]=1

Participants

4

Reactant 3

HCID 9260PyrimidineHCID 160693Formamidine acetateHCID 103523512-benzoylpyrimidine

Product 1

HCID 178516499HCID 178516499, compound

Procedure

As is discussed PCT publication WO 95/29898, compounds of formula I may be made using the following general procedure. First, a benzoyl chloride is reacted with the magnesium enolate of an appropriate β-ketoester to form a triketo intermediate followed by hydrolysis and decarboxylation to a β-diketone intermediate. The diketone is then converted to the alkoxy methylene or dialkylaminomethylene β-diketone by standard methods. Final ring closure to the pyrimidine is accomplished by heating with formamidine acetate in an alcoholic solvent, followed by reduction of the resulting benzoyl pyrimidine, to produce a hydroxybenzyl pyrimidine compound.

Sources & evidence

ORD record
ord-65b553bc365a44e18c9c007780afa36e
Source dataset
uspto-grants-1999_07
Patent number
US05925795

Reaction notes

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