M-Cresol → Methyl 4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate

HRID 1078190Notes

Reaction equation

HRID 1078190 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.[CH:15]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O.CCOCC>[CH3:22][C:16]1[CH:15]=[C:20]([CH:19]=[CH:18][CH:17]=1)[O:21][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

Participants

7

Reactant 4

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 54047637Methyl 2-(4-chloro-6-methoxypyrimidin-5-yl)acetate

Product 1

HCID 54458061Methyl 4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-chloro-6-methoxy-pyrimidin-5-yl-acetate (21.7 g, 100 mmol), m-cresol (10.8 g, 100mmol), 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, extraction with ether and drying gives the methyl 4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate as an oil.

Workup

  1. customdrying

Sources & evidence

ORD record
ord-5d85b40b8b3f4115bf535043f14a9bee
Source dataset
uspto-grants-1996_08
Patent number
US05547919

Reaction notes

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