Water → HCID 67026756, compound

HRID 12089Notes

Reaction equation

HRID 12089 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:10][CH3:11])[CH3:9])[C:5]([Cl:12])=[CH:4][N:3]=1.[N+:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:12][C:5]1[C:6]([N:8]([CH2:10][CH3:11])[CH3:9])=[N:7][C:2]([O:23][C:19]2[CH:20]=[C:21]([CH3:22])[C:16]([N+:13]([O-:15])=[O:14])=[CH:17][C:18]=2[CH3:24])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2821102,5-Dimethyl-4-nitrophenolHCID 79631958HCID 79631958, compound

Product 1

HCID 67026756HCID 67026756, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 16.8 g (40 mmol) 2,5-dichloro-N-ethyl-N-methylpyrimidin-4-amine, 7.35 g 4-nitro-2,5-dimethylphenol (44 mmol) and 8.29 g potassium carbonate (60 mmol) in 70 ml DMF were stirred for 20 hrs at 100° C. After adding the mixture to 150 ml water the resulting suspension was extracted twice with 50 ml dichloromethane. The combined organic layers were washed with aqueous solution of sodium hydroxide. The organic layer was dried over magnesium sulfate, concentrated in vacuo and column chromatography (dichloromethane) yielded 8.3 g (47%) with a purity of 76%; log P (pH=2.3)=4.07.

Workup

  1. extractionwas extracted twice with 50 ml dichloromethane
  2. washThe combined organic layers were washed with aqueous solution of sodium hydroxide
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo and column chromatography (dichloromethane)
  5. customyielded 8.3 g (47%) with a purity of 76%

Sources & evidence

ORD record
ord-aa3196a16d9a4431bf69a02926667947
Source dataset
uspto-grants-2010_06
Patent number
US07727986B2

Reaction notes

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