Sodium hydride → HCID 178422572, compound

HRID 1805848Notes

Reaction equation

HRID 1805848 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=2)[CH2:3][CH2:2]1.[H-].[Na+].[Cl:15][C:16]1[N:24]=[C:23]2[C:19]([NH:20][CH:21]=[N:22]2)=[C:18](Cl)[N:17]=1>>[Cl:15][C:16]1[N:24]=[C:23]2[C:19]([N:20]=[CH:21][NH:22]2)=[C:18]([O:11][C:7]2[C:6]([CH3:12])=[CH:5][C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:8]=2[CH3:10])[N:17]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 53244122,6-DichloropurineHCID 576935554-Cyclopropyl-2,6-dimethylphenol

Product 1

HCID 178422572HCID 178422572, compoundYield 67.1%

Procedure

To a solution of 4-cyclopropyl-2,6-dimethylphenol (263 mg, 1.62 mmol) in 1-methyl-2-pyrridone (3 mL) at 0° C. was added NaH (65 mg, 1.62 mmol). The reaction mixture was stirred at room temperature for 30 min and a solution of 2,6-dichloropurine (102 mg, 0.54 mmol) in 1-methyl-2-pyrridone (2 mL) was added to the mixture. The mixture was heated at 100° C. for 16 h and then cooled to room temperature. The reaction was poured into ice water and extracted with CHCl3 (3×20 mL). The combined organic solution was washed with H2O (20 mL) and brine (20 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (MeOH:CHCl3=5:95) yielded 114 mg (67%) of 2-chloro-6-(4-cyclopropyl-2,6-dimethylphenoxy)-9H-purine.

Workup

  1. temperatureThe mixture was heated at 100° C. for 16 h
  2. temperaturecooled to room temperature
  3. extractionextracted with CHCl3 (3×20 mL)
  4. washThe combined organic solution was washed with H2O (20 mL) and brine (20 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cf04bb00c50d441689e3d46edd24d288
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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