2-Butyn-1-ol → HCID 17979094, compound

HRID 1354158Notes

Reaction equation

HRID 1354158 reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:9])([CH:6]([OH:8])[CH3:7])[CH3:5].Cl[C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.[CH2:18]([OH:22])[C:19]#[C:20][CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH2:18]([O:22][C:11]1[CH:16]=[C:15]([O:8][CH:6]([CH3:7])[C:4]([OH:9])([CH3:5])[CH3:3])[N:14]=[CH:13][N:12]=1)[C:19]#[C:20][CH3:21]

Participants

7

Reactant 5

HCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 953622-Methylbutane-2,3-diol

Product 1

HCID 17979094HCID 17979094, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 5 ml of tetrahydrofuran was suspended 0.24 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.26 g of 2-methylbutan-2,3-diol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.38 g of 4,6-dichloropyrimidin in tetrahydrofuran, followed by stirring at 0° C. for 4 hours. To this was added dropwise 0.4 ml of a solution containing 0.20 g of 2-butyn-1-ol and further added 0.12 g of sodium hydride (60% in oil), followed by stirring at room temperature for 3.5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with 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 0.41 g of 4-(2-butynyloxy)-6-(2-hydroxy-1,2-dimethylpropyloxy)pyrimidine.

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at 0° C. for 4 hours
  3. stirringby stirring at room temperature for 3.5 hours
  4. extractionwas extracted three times with t-butyl methyl ether
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a6ba0cb54fe47a3a6766af1cd2fc55b
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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