Sodium hydride → HCID 68797967, compound

HRID 2233325Notes

Reaction equation

HRID 2233325 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[H-].[Na+].Cl[C:11]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:13][N:12]=1>O1CCOCC1.CC(OC)(C)C>[CH2:1]([O:7][C:11]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:13][N:12]=1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 699635-Hexen-1-olHCID 126742762-Chloro-4,5-diphenylpyrimidine

Product 1

HCID 68797967HCID 68797967, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

1.50 g (15 mmol) of 5-hexen-1-ol dissolved in 30 ml of dioxane were mixed with 600 mg (60%, 15 mmol) of sodium hydride and stirred at room temperature for 30 minutes. Addition of 1.7 g (7.5 mmol) of 2-chloro-4,5-diphenylpyrimidine was followed by stirring at room temperature for 6 hours. Taking up in MTBE and washing with saturated NaCl solution were followed by drying over sodium sulfate and evaporation. The residue was purified on silica gel with heptane/ethyl acetate (15:1). 1.93 g (77%) of the desired product were obtained.

Workup

  1. stirringby stirring at room temperature for 6 hours
  2. washwashing with saturated NaCl solution
  3. dry with materialby drying over sodium sulfate and evaporation
  4. customThe residue was purified on silica gel with heptane/ethyl acetate (15:1)

Sources & evidence

ORD record
ord-539dec8543fc4db89ad8a2ce2dd55f5c
Source dataset
uspto-grants-2010_05
Patent number
US07709494B2

Reaction notes

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