Propargyl alcohol → HCID 22599782, compound

HRID 1592118Notes

Reaction equation

HRID 1592118 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].Cl[C:8]1[CH:13]=[C:12](Cl)[N:11]=[CH:10][N:9]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:6][C:8]1[CH:13]=[C:12]([O:6][CH2:3][C:4]#[CH:5])[N:11]=[CH:10][N:9]=1)[C:4]#[CH:5]

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 22599782HCID 22599782, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 4 ml of tetrahydrofuran was suspended 0.27 g of sodium hydride (60% in oil), to which 0.7 ml of a tetrahydrofuran solution containing 0.33 g of 2-propyn-1-ol was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes and then cooled to 0° C., to which 0.7 ml of a tetrahydrofuran solution containing 0.4 g of 4,6-dichloropyrimidine was slowly added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 40 minutes. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.35 g of 4,6-bis(2-propynyloxy)pyrimidine (the present compound (52)), m.p.: 74.0° C.

Workup

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. additionAfter completion of the dropwise addition
  5. stirringthe mixture was stirred at room temperature for 40 minutes
  6. extractionextracted three times with chloroform
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b41ab7b7925f4ca3aaf821a7d46111a0
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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