2,2-Dimethyl-3-pentanol → HCID 17979100, compound

HRID 1354146Notes

Reaction equation

HRID 1354146 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:10])([CH:6]([OH:9])[CH2:7][CH3:8])[CH3:5].[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:9][CH:6]([CH2:7][CH3:8])[C:4]([CH3:10])([CH3:5])[CH3:3])[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 198712,2-Dimethyl-3-pentanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979100HCID 17979100, 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 tetrahydrofuran containing 0.26 g of 2,2-dimethyl-3-pentanol dissolved therein was added dropwise at room temperature, 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 at 0° C., followed by stirring at the same temperature for 1 hour and 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, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.35 g of 4-chloro-6-(1-ethyl-2,2-dimethylpropyloxy)pyrimidine.

Workup

  1. additiontherein was added dropwise at room temperature
  2. dissolutiondissolved
  3. customat 0° C.
  4. stirringby stirring at the same temperature for 1 hour and at room temperature for 4 hours
  5. extractionwas extracted three times with t-butyl methyl ether
  6. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-75897a72b9cd43588a210c0796ebb9f9
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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