Sodium hydride → HCID 17979083, compound

HRID 1354113Notes

Reaction equation

HRID 1354113 reaction equation
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]([C:9]([F:12])([F:11])[F:10])([CH3:8])[CH2:6][OH:7].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[N:19]=[CH:18][N:17]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:15][C:16]1[CH:21]=[C:20]([O:7][CH2:6][C:5]([C:9]([F:11])([F:10])[F:12])([C:4]([F:13])([F:14])[F:3])[CH3:8])[N:19]=[CH:18][N:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 27361853,3,3-Trifluoro-2-methyl-2-(trifluoromethyl)propan-1-ol

Product 1

HCID 17979083HCID 17979083, compound

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 0.44 g of 2,2-bis(trifluoromethyl)propanol 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 1.5 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-[2,2-bis(trifluoromethyl)propoxy]pyrimidine.

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at the same temperature for 1.5 hours
  3. extractionwas extracted three times with t-butyl methyl ether
  4. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-aaa4e59837a94842b44ac3776c5ca36f
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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