2-Butyn-1-ol → 4-(2-Butynyloxy)-6-(1,3-dimethylbutyloxy)pyrimidine

HRID 1354108Notes

Reaction equation

HRID 1354108 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]([CH3:21])[CH2:17][CH:18]([CH3:20])[CH3:19])[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]([CH3:21])[CH2:17][CH:18]([CH3:20])[CH3:19])[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 179790854-Chloro-6-(1,3-dimethylbutoxy)pyrimidine

Product 1

HCID 179791204-(2-Butynyloxy)-6-(1,3-dimethylbutyloxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 3.5 ml of tetrahydrofuran was suspended 0.1 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.16 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 the above 4-chloro-6-(1,3-dimethylbutoxy)pyrimidine in tetrahydrofuran, followed by stirring at room temperature for 4 hour. 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 resulting residue was subjected to silica gel column chromatography to give 0.30 g of 4-(2-butynyloxy)-6-(1,3-dimethylbutyloxy)pyrimidine (the present compound (5)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at room temperature for 4 hour
  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-7d3421bae6814fd3b7815d1e31cfefa9
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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