Sodium hydride → 4-Chloro-6-(1,3,3-trimethylbutoxy)pyrimidine

HRID 1354110Notes

Reaction equation

HRID 1354110 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH3:7].[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:8][CH:6]([CH3:7])[CH2:5][C:4]([CH3:10])([CH3:9])[CH3:3])[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 1107894,4-Dimethylpentan-2-ol

Product 1

HCID 179790904-Chloro-6-(1,3,3-trimethylbutoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.24 g of 4,4-dimethyl-2-pentanol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 2 hours and further stirring at room temperature for 4 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 and dried over anhydrous magnesium sulfate to give a crude product of 4-chloro-6-(1,3,3-trimethylbutoxy)pyrimidine.

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at the same temperature for 2 hours
  3. stirringfurther stirring at room temperature for 4 hours
  4. extractionwas extracted three times with t-butyl methyl ether
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-d5032e01a14241cba181feffd45f50b7
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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