2-Butyn-1-ol → HCID 17979082, compound

HRID 1354141Notes

Reaction equation

HRID 1354141 reaction equation
[H-].[Na+].[Cl:3][CH:4]([Cl:11])[CH:5]([OH:10])[C:6]([CH3:9])([CH3:8])[CH3:7].Cl[C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1.[CH2:20]([OH:24])[C:21]#[C:22][CH3:23].[Cl-].[NH4+]>O1CCCC1>[CH2:20]([O:24][C:13]1[CH:18]=[C:17]([O:10][CH:5]([CH:4]([Cl:11])[Cl:3])[C:6]([CH3:9])([CH3:8])[CH3:7])[N:16]=[CH:15][N:14]=1)[C:21]#[C:22][CH3:23]

Participants

7

Reactant 5

HCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 12533987HCID 12533987, compound

Product 1

HCID 17979082HCID 17979082, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 3 ml of tetrahydrofuran was suspended 0.09 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.31 g of 1,1-dichloro-3,3-dimethyl-2-butanol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.27 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 2.5 hours. To this was added dropwise 0.4 ml of a solution containing 0.15 g of 2-butyn-1-ol in tetrahydrofuran at room temperature and further added 0.09 g of sodium hydride (60% in oil), followed by stirring for 4 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 0.45 g of 4-(2-butynyloxy)-6-(1-(dichloromethyl)-2,2-dimethylpropyloxy)pyrimidine (the present compound (39)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringby stirring at the same temperature for 2.5 hours
  3. stirringby stirring for 4 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-b9dc62bb1ca44393870558e97823b25d
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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