Dimethylformamide → HCID 11230310, compound

HRID 1397632Notes

Reaction equation

HRID 1397632 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N:6]2.[CH3:17]N(C=O)C.[H-].[Na+].CI>>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[N:6]2[CH3:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15363167HCID 15363167, compound

Product 1

HCID 11230310HCID 11230310, compound

Procedure

To a solution of 6-chloro-8-phenyl-7H-purine (0.200 g, 0.000867 mol) (Example 109, step a) in DMF (8.0 mL, 0.10 mol) was added sodium hydride (0.025 g, 0.0010 mol). The mixture was stirred for 20 minutes and to this was added methyl iodide (0.065 mL, 0.0010 mol) and the mixture was stirred for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl, and the mixture was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (3 to 10% acetone/toluene) to obtain 145 mg (68%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customThe reaction was quenched by addition of saturated aqueous NH4Cl
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (3 to 10% acetone/toluene)
  9. customto obtain 145 mg (68%)

Sources & evidence

ORD record
ord-122e732abd3045709a63cf3df12fc2f6
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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