Sodium hydride → HCID 17979099, compound

HRID 1354153Notes

Reaction equation

HRID 1354153 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]#[C:5][CH2:6][CH3:7].Cl[C:10]1[N:15]=[CH:14][N:13]=[C:12]([O:16][CH:17]([CH3:22])[C:18]([CH3:21])([OH:20])[CH3:19])[CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:8][C:10]1[CH:11]=[C:12]([O:16][CH:17]([CH3:22])[C:18]([OH:20])([CH3:19])[CH3:21])[N:13]=[CH:14][N:15]=1)[C:4]#[C:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 804212-Pentyn-1-olHCID 17979112HCID 17979112, compound

Product 1

HCID 17979099HCID 17979099, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 3 ml of tetrahydrofuran was suspended 0.17 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.17 g of 2-pentyn-1-ol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of tetrahydrofuran containing 0.37 g of 3-(6-chloro-4-pyrimidyloxy)-2-methyl-2-butanol dissolved therein, followed by stirring at the same temperature for 1 hour and 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 0.33 g of 4-(2-pentynyloxy)-6-(2-hydroxy-1,2-dimethylpropyloxy)pyrimidine.

Workup

  1. additionwas added dropwise at 0° C.
  2. dissolutiondissolved
  3. stirringby stirring at the same temperature for 1 hour and 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-24f2451db6b74b07b38fbaa097ab6675
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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