Methanol → HCID 14327548, compound

HRID 981478Notes

Reaction equation

HRID 981478 reaction equation
[CH3:1][OH:2].C[O-].[Na+].Cl[C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:8]=1.O>CN(C)C=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:9]2[N:8]=[C:7]([O:2][CH3:1])[CH:12]=[C:11]([CH3:13])[N:10]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 43459964-Chloro-N-(4-chlorophenyl)-6-methylpyrimidin-2-amineHCID 10942334Sodium Methoxide

Product 1

HCID 14327548HCID 14327548, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A 28% methanol solution of sodium methylate (1.5 g) was added to a solution of 1.5 g of 4-chloro-2-(4-chloroanilino)-6-methylpyrimidine in 50 ml of dimethylformamide and the mixture was stirred for 2 hours at 70° C. After completion of the reaction, the reaction mixture was poured into water, extracted with 150 ml of toluene, washed with water, dried over Glauber's salt, and the toluene layer was concentrated by evaporation. The residue was purified by silica gel column chromatography to obtain 1.3 g (yield: 88%) of 2-(4-chloroanilino)-4-methoxy-6-methylpyrimidine having a melting point of 101°-103° C.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with 150 ml of toluene
  3. washwashed with water
  4. dry with materialdried over Glauber's salt
  5. concentrationthe toluene layer was concentrated by evaporation
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4be989f880524bffa43f898f9952bf2a
Source dataset
uspto-grants-1991_02
Patent number
US04992438

Reaction notes

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