3-Methylpentan-2-ol → HCID 17979109, compound

HRID 1354120Notes

Reaction equation

HRID 1354120 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH2:8][CH3:9])[CH:5]([OH:7])[CH3:6].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:7][CH:5]([CH3:6])[CH:4]([CH3:3])[CH2:8][CH3:9])[N:14]=[CH:13][N:12]=1)[C:19]#[C:20][CH3:21]

Participants

7

Reactant 5

HCID 112613-Methylpentan-2-olHCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979109HCID 17979109, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.21 g of 3-methyl-2-pentanol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was slowly added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.4 ml of a solution containing 0.14 g of 2-butyn-1-ol at 0° C. and further added 0.10 g of sodium hydride (60% in oil), followed by further stirring at room temperature 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 0.29 g of 4-(2-butynyloxy)-6-(1,2-dimethylbutyloxy)pyrimidine (the present compound (16)).

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at the same temperature for 3 hours
  3. stirringby further stirring at room temperature 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-c34faee805b5485eb3815e26ae110c01
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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