Water → HCID 17979078, compound

HRID 1354164Notes

Reaction equation

HRID 1354164 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH:14]([CH3:19])[C:15](O)([CH3:17])[CH3:16])[N:10]=[CH:9][N:8]=1)[C:2]#[C:3][CH2:4][CH3:5].N1C=CC=CC=1.S(Cl)(Cl)=O.O>C(Cl)(Cl)Cl>[CH2:1]([O:6][C:7]1[CH:12]=[C:11]([O:13][CH:14]([CH3:19])[C:15]([CH3:17])=[CH2:16])[N:10]=[CH:9][N:8]=1)[C:2]#[C:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 17979099HCID 17979099, compound

Product 1

HCID 17979078HCID 17979078, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 3 ml of chloroform was dissolved 0.5 g of 4-(2-pentynyloxy)-6-(2-hydroxy-1,2-dimethylpropyloxy)pyrimidine, to which 0.18 g of pyridine was added and 0.27 g of thionyl chloride was added dropwise at −13° C., followed by stirring for 1.5 hours. The reaction mixture was then poured into water, which was extracted three times with chloroform. The combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate solution, 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 0.3 g of 4-(2-pentynyloxy)-6-(1,2-dimethyl-2-propenyloxy)pyrimidine.

Workup

  1. extractionwas extracted three times with chloroform
  2. washThe combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-519ec6c654064517ae0b45a23d2a3811
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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