Water → HCID 17979075, compound

HRID 1354161Notes

Reaction equation

HRID 1354161 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([O:12][CH:13]([CH3:18])[C:14]([CH3:17])(O)[CH3:15])[CH:7]=1)[C:2]#[C:3][CH3:4].N1C=CC=CC=1.S(Cl)(Cl)=O.O>C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([O:12][CH:13]([CH3:18])[C:14]([CH3:17])=[CH2:15])[N:9]=[CH:10][N:11]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 17979094HCID 17979094, compound

Product 1

HCID 17979075HCID 17979075, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 3 ml of chloroform was dissolved 0.42 g of 3-[6-(2-butynyloxy)pyrimidin-4-yloxy]-2-methyl-2-butanol, to which 0.2 g of pyridine was added and 0.15 ml of thionyl chloride was added dropwise at −13° C., followed by stirring 2 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, 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 0.23 g of 4-(2-butynyloxy)-6-(1,2-dimethylallyloxy)pyrimidine.

Workup

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

Sources & evidence

ORD record
ord-d1a50ee2f9a7411aa50298f69b474937
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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