2-Butyn-1-ol → HCID 17979097, compound

HRID 1354106Notes

Reaction equation

HRID 1354106 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([O:15][CH:16]([CH2:21][CH3:22])[C:17]([CH3:20])([CH3:19])[CH3:18])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([O:15][CH:16]([CH2:21][CH3:22])[C:17]([CH3:19])([CH3:18])[CH3:20])[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 17979100HCID 17979100, compound

Product 1

HCID 17979097HCID 17979097, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 3 ml of tetrahydrofuran was suspended 0.08 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.12 g of 2-butyn-1-ol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.35 g of 4-chloro-6-(1-ethyl-2,2-dimethylpropyloxy)pyrimidine in tetrahydrofuran at room temperature, followed by stirring for 6 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 0.22 g of 4-(2-butynyloxy)-6-(1-ethyl-2,2-dimethylpropyloxy)pyrimidine (the present compound (4)).

Workup

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

Sources & evidence

ORD record
ord-4427faa470e640a784b4d830531c0d08
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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