3,3-Dimethyl-2-butanol → HCID 17979071, compound

HRID 1354145Notes

Reaction equation

HRID 1354145 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[CH:5]([OH:7])[CH3:6].[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][CH:5]([CH3:6])[C:4]([CH3:9])([CH3:8])[CH3:3])[N:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 100453,3-Dimethyl-2-butanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979071HCID 17979071, 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 0.23 g of 3,3-dimethyl-2-butanol 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, followed by stirring at the same temperature for 6 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 0.24 g of 4-chloro-6-(1,2,2-trimethylpropyloxy)pyrimidine.

Workup

  1. additiontherein was added dropwise at room temperature
  2. dissolutiondissolved
  3. stirringby stirring at the same temperature for 6 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-1b5013c3fc1d408f8ed3144e2f85067c
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

Loading…