3,3-Dimethyl-1-butanol → HCID 17979066, compound

HRID 1354149Notes

Reaction equation

HRID 1354149 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][OH:7].[Cl:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:10][C:11]1[CH:16]=[C:15]([O:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH3:3])[N:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 122333,3-Dimethyl-1-butanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979066HCID 17979066, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 0.23 g of 3,3-dimethyl-1-butanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same 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, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.41 g of 4-chloro-6-(3,3-dimethylbutyloxy)pyrimidine.

Workup

  1. additionwas added dropwise at 0° C.
  2. dissolutiondissolved
  3. stirringby stirring at the same 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
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9ec67b617f9041e2962bf77e3a75f251
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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