Sodium hydride → 4-Chloro-6-(2,2-dichloropropyloxy)pyrimidine

HRID 1354162Notes

Reaction equation

HRID 1354162 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]([Cl:14])([CH3:13])[CH2:11][OH:12].[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[Cl:8][C:6]1[CH:7]=[C:2]([O:12][CH2:11][C:10]([Cl:14])([Cl:9])[CH3:13])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 18314644HCID 18314644, compound

Product 1

HCID 179791184-Chloro-6-(2,2-dichloropropyloxy)pyrimidineYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 0.23 g of 4,6-dichloropyrimidine and 0.2 g of 2,2-dichloro-1-propanol were dissolved in 2 ml of tetrahydrofuran, to which 0.07 g of sodium hydride (60% in oil) was added at 0° C., followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel chromatography to give 0.18 g of 4-chloro-6-(2,2-dichloropropyloxy)pyrimidine.

Workup

  1. additionwas added at 0° C.
  2. extractionwas extracted three times with t-butyl methyl ether
  3. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4dbfee7340104fe1bd40988aae08347e
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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