2-Butyn-1-ol → 4-(2-Butynyloxy)-6-chloropyrimidine

HRID 1759956Notes

Reaction equation

HRID 1759956 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:8][C:9]1[CH:14]=[C:13]([O:7][CH2:3][C:4]#[C:5][CH3:6])[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 121376024-(2-Butynyloxy)-6-chloropyrimidineYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 24 ml of tetrahydrofuran was suspended 1.05 g of sodium hydride (60% in oil), to which 8 ml of a tetrahydrofuran solution containing 1.42 g of 2-butyn-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 8 ml of a tetrahydrofuran solution containing 3 g of 4,6-dichloropyrimidine was slowly added dropwise, followed by further stirring at 0° C. for 4 hours. 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 3.16 g of 4-chloro-6-(2-butynyloxy)pyrimidine, m.p.: 43.5° C.

Workup

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. stirringby further stirring at 0° C. for 4 hours
  5. extractionextracted three times with chloroform
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2730e9080d2e4d8493431a1b851bb1d8
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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