Sodium hydride → Sodium 1,6-dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylate

HRID 25867Notes

Reaction equation

HRID 25867 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:6](=[O:11])[C:7]=1[C:8]([OH:10])=[O:9].CC1N=CN(C2C=CC(C)=CC=2)C(=O)C=1C(OCC)=O.[H-].[Na+:40]>C(COC)OC.CCOCC>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[C:6](=[O:11])[C:7]=1[C:8]([O-:10])=[O:9].[Na+:40]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 213254901,6-Dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylic acidHCID 21325495Ethyl 1,6-dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylate

Product 1

HCID 23684865Sodium 1,6-dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 8.0 g (0.033 mole) of 1,6-dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylic acid, prepared from ethyl 1,6-dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylate by the hydrolysis method of Example 2, and one equivalent of sodium hydride (added as mineral oil dispersion), slurried in 300 ml of glyme is stirred at ambient temperature for 3 days. The solid product is isolated by filtration, slurried in ether and reisolated to give after drying 5.0 g (57% yield) of sodium 1,6-dihydro-4-methyl-6-oxo-1-(4-tolyl)pyrimidine-5-carboxylate, m.p. 208°-10° C. dec.

Workup

  1. customThe solid product is isolated by filtration
  2. customto give

Sources & evidence

ORD record
ord-3daef18a793e446e9d422b3c51603dd1
Source dataset
uspto-grants-1979_04
Patent number
US04147528

Reaction notes

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