Sodium Carbonate → HCID 14281147, compound

HRID 2231648Notes

Reaction equation

HRID 2231648 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[N:10]=2)[N:3]=1.P(Cl)(Cl)([Cl:24])=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:24][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[N:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178424498HCID 178424498, compound

Product 1

HCID 14281147HCID 14281147, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To solution of 4-hydroxy-6-methyl-2-(6-m-tolyl-2-pyridinyl)pyrimidine (5 g) in toluene (100 ml), was added phosphoryl chloride (5 g). The mixture was heated under refluxing for one hourand left to stand to room temperature. Aqueous sodium carbonate solution was added thereto until the reaction solution became about pH 8 to be separated into two layers. Toluene layer was washed with water and dried over anhydrous magnesium sulfate. The toluene layer was concentrated under reduced pressure to obtain 4-chloro-6-methyl-2-(6-m-tolyl-2-pyridinyl)pyrimidine (4.9 g, yield 92%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for one hourand
  3. waitleft
  4. customto stand to room temperature
  5. customto be separated into two layers
  6. washToluene layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe toluene layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-78da1593d0fa41669a217a40c014322f
Source dataset
uspto-grants-1988_11
Patent number
US04783466

Reaction notes

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