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

HRID 1759965Notes

Reaction equation

HRID 1759965 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([S:15][CH3:16])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([S:15][CH3:16])[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 218130774-Chloro-6-(methylsulfanyl)pyrimidine

Product 1

HCID 225998774-(2-Butynyloxy)-6-methylthiopyrimidineYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 10 ml of tetrahydrofuran was suspended 0.41 g of sodium hydride (60% in oil), to which 2 ml of a tetrahydrofuran solution containing 0.58 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, to which 2 ml of a tetrahydrofuran solution containing 1.1 g of 4-chloro-6-methylthiopyrimidine was slowly added dropwise, followed by further stirring 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 1.3 g of 4-(2-butynyloxy)-6-methylthiopyrimidine.

Workup

  1. additionwas slowly added dropwise
  2. additionwas slowly added dropwise
  3. stirringby further stirring for 4 hours
  4. extractionextracted three times with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b0bf0dc174143389d4466001a930bf9
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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