Neopentyl alcohol → HCID 17979113, compound

HRID 1354147Notes

Reaction equation

HRID 1354147 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:9][C:10]1[CH:15]=[C:14]([O:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH3:3])[N:13]=[CH:12][N:11]=1

Participants

6

Procedure

In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.5 ml of tetrahydrofuran containing 0.14 g of 2,2-dimethyl-1-propanol 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 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 0.16 g of 4-chloro-6-(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 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-e84410401dde484c9117e5d332b75559
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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