Hydrochloric Acid → 4-Bromo-2-(4-fluorophenylamino)-5,6-dimethylpyrimidine

HRID 1604023Notes

Reaction equation

HRID 1604023 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(Br)(Br)[Br:19].[OH-].[Na+].Cl>CN(C)C=O>[Br:19][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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 178433118HCID 178433118, compound

Product 1

HCID 211916914-Bromo-2-(4-fluorophenylamino)-5,6-dimethylpyrimidineYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

5 g(21.44 mmole) of 2-(4-fluorophenylamino)-4-hydroxy-5,6-dimethylpyrimidine produced in Example 1 was suspended in 40 ml of N,N-dimethylformamide and the resulting suspension was warmed to 65° C. 8.1 g(30 mmole) of phosphorus tribromide was added dropwise thereto over 20 minutes and the resulting mixture was allowed to react at 75° C. for 30 minutes. The reaction solution was cooled to room temperature, poured onto 500 g of ice-water, adjusted to pH 11 with sodium hydroxide solution, stirred for 30 minutes and then adjusted again to pH 5.5 with dilute hydrochloric acid. The resulting yellow solid product was washed with 100 ml of water and the dried to obtain 4.1 g of the title compound.

Workup

  1. customto react at 75° C. for 30 minutes
  2. temperatureThe reaction solution was cooled to room temperature
  3. washThe resulting yellow solid product was washed with 100 ml of water
  4. customthe dried

Sources & evidence

ORD record
ord-a300a657a30c4696b508d0e90379b004
Source dataset
uspto-grants-1999_11
Patent number
US05990311

Reaction notes

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