3-Hydroxyacetophenone → Methyl 4-(3-acetylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate

HRID 1957168Notes

Reaction equation

HRID 1957168 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([O:13][CH3:14])[N:5]=[CH:4][N:3]=1.[CH3:15][C:16]([C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([OH:24])[CH:23]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[C:16]([C:18]1[CH:23]=[C:22]([CH:21]=[CH:20][CH:19]=1)[O:24][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([O:13][CH3:14])[N:5]=[CH:4][N:3]=1)(=[O:17])[CH3:15]

Participants

6

Reactant 4

HCID 84873-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 54047637Methyl 2-(4-chloro-6-methoxypyrimidin-5-yl)acetate

Product 1

HCID 53697352Methyl 4-(3-acetylphenoxy)-6-methoxy-pyrimidin-5-yl-acetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-chloro-6-methoxy-pyrimidin-5-yl-acetate (21.7 g, 100 mmol), 3-hydroxyacetophenone (13.6 g, 100 mmol), potassium carbonate (20.7 g, 150 mmol) and a catalytic amount of 18-crown-6 in dimethylformamide (50 ml) is heated to +120° C. for 1 hour. Addition of crushed ice, filtration and drying gives the methyl 4-(3-acetylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate (28.5 g) having a m.p. of 65°-67° C.

Workup

  1. additionAddition of crushed ice, filtration
  2. customdrying

Sources & evidence

ORD record
ord-ab7a09881fff4928a658579598da3410
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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