2-Butyn-1-ol → HCID 17979102, compound

HRID 1354122Notes

Reaction equation

HRID 1354122 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]([CH3:22])[CH:17]([O:20][CH3:21])[O:18][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]([CH3:22])[CH:17]([O:18][CH3:19])[O:20][CH3:21])[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 17979072HCID 17979072, compound

Product 1

HCID 17979102HCID 17979102, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 1.5 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.05 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 0.16 g of 4-chloro-6-(2,2-dimethoxy-1-methylethoxy)pyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 1 hour and further stirring at room temperature for 3 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 0.11 g of 4-(2-butynyloxy)-6-(2,2-dimethoxy-1-methylethoxy)pyrimidine (the present compound (18)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at the same temperature for 1 hour
  3. stirringfurther stirring at room temperature for 3 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-627a30c73ff84c169033f56f7c7a868c
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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