Sodium Carbonate → 4-Chloro-6-methyl-2-(6-n-propyl-2-pyridinyl)pyrimidine

HRID 580322Notes

Reaction equation

HRID 580322 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]([CH2:15][CH2:16][CH3:17])[N:10]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:20][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH3:17])[N:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178438999HCID 178438999, compound

Product 1

HCID 142532544-Chloro-6-methyl-2-(6-n-propyl-2-pyridinyl)pyrimidineYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To solution of 4-hydroxy-6-methyl-2-(6-n-propyl-2-pyridinyl)pyrimidine (2 g) in toluene (20 ml), was added phosphoryl chloride (2 g). The mixture was heated under refluxing for one hour and 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 collected and 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-n-propyl-2-pyridinyl)pyrimidine (2.03 g).

Workup

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

Sources & evidence

ORD record
ord-ba9259d5a13e4010b2a2acdfb0169958
Source dataset
uspto-grants-1988_06
Patent number
US04752608

Reaction notes

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