Sodium Hydroxide → 4-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine

HRID 1604022Notes

Reaction equation

HRID 1604022 reaction equation
O[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O.[OH-].[Na+]>CN(C)C=O>[Cl:20][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178433118HCID 178433118, compound

Product 1

HCID 99923764-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amineYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

40.5 g(174.1 mmole) of 2-(4-fluorophenylamino)-4-hydroxy-5,6-dimethylpyrimidine produced in Example 1 was suspended in 80 ml of N,N-dimethylformamide and the resulting suspension was heated to 80° C. 31.9 g(19.4 ml, 210.1 mmole) of phosphorus oxychloride was added thereto over one hour at constant temperature of 85° C. The reaction solution was stirred for 30 minutes and then 400 g of ice-water was added thereto with stirring. The mixture was adjusted to pH 11 by adding sodium hydroxide and then the resulting solid product was filtered. The separated solid product was washed with 150 ml of 50% aqueous methanol solution and then dried to obtain 42.3 g of the title compound.

Workup

  1. stirringwith stirring
  2. filtrationthe resulting solid product was filtered
  3. washThe separated solid product was washed with 150 ml of 50% aqueous methanol solution
  4. customdried

Sources & evidence

ORD record
ord-d0e5a81381754c5fae4c7d71f906caaa
Source dataset
uspto-grants-1999_11
Patent number
US05990311

Reaction notes

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