Sodium Hydroxide → 4-Chloro-6-methyl-2-(propan-2-yl)pyrimidine

HRID 14345

Reaction equation

HRID 14345 reaction equation
[CH:1]([C:4]1[N:9]=[C:8](O)[CH:7]=[C:6]([CH3:11])[N:5]=1)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:14])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:14][C:8]1[CH:7]=[C:6]([CH3:11])[N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178419104HCID 178419104, compound

Product 1

HCID 33069074-Chloro-6-methyl-2-(propan-2-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

76.1 g of 2-isopropyl-6-methyl-4-pyrimidinol [2814-20-2] (500 mmol) are dissolved in 300 ml of toluene at 90° C. 80.5 g of phosphorus oxychloride (525 mmol) are added dropwise thereto at from 90 to 103° C., and the reaction mixture is heated at 110° C. for 2 hours. After cooling to 20° C., the reaction mixture is adjusted to pH 8 using 4M sodium hydroxide solution, with cooling. The aqueous phase is separated off and extracted with 100 ml of toluene. The combined organic phases are washed three times with 100 ml of water each time and dried at RT under 2 mbar. 89.7 g (105%; contains toluene) are obtained.

Workup

  1. temperatureAfter cooling to 20° C.
  2. temperaturewith cooling
  3. customThe aqueous phase is separated off
  4. extractionextracted with 100 ml of toluene
  5. washThe combined organic phases are washed three times with 100 ml of water each time
  6. customdried at RT under 2 mbar
  7. custom89.7 g (105%; contains toluene) are obtained

Sources & evidence

ORD record
ord-c1733baf1fbe4d7cba07485c4f3375fa
Source dataset
uspto-grants-2010_06
Patent number
US07731985B2

Linked notes

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