Citric Acid → 4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

HRID 431063Notes

Reaction equation

HRID 431063 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([O:22]CC)=[O:21])=[CH:5][N:4]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>CS(C)=O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([OH:22])=[O:21])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22025927Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 226655724-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acidYield 100.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A suspension of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (2.00 g) obtained in Example 1 (1) in dimethylsulfoxide (10 ml) is treated with 10% aqueous sodium hydroxide solution (10 ml) at room temperature. To the reaction mixture is added dimethylsulfoxide (5 ml), and the mixture is stirred at room temperature overnight. To the resulting colorless solution is added citric acid until the solution becomes acidic. To the solution is added an excess amount of water (about 50 ml), and the resulting precipitates are collected by filtration. The precipitates are washed with isopropyl alcohol and isopropyl ether successively, and dried under reduced pressure to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-carboxypyrimidine (1.864 g) as pale yellow impalpable powder, m.p. 238-240° C. (dec.).

Workup

  1. customthe resulting precipitates
  2. filtrationare collected by filtration
  3. washThe precipitates are washed with isopropyl alcohol and isopropyl ether successively
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3bdfd20bc7f947bb91168927e79cd5c0
Source dataset
uspto-grants-2003_12
Patent number
US06656935B2

Reaction notes

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