Sodium hydride → HCID 68859476, compound

HRID 1783533Notes

Reaction equation

HRID 1783533 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH2:12][C:13]2[C:14]([NH2:21])=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[H-].[Na+].[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>CN(C)C=O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([N:11]2[CH2:12][C:13]3[C:14](=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=3)[NH:21][C:24]2=[O:25])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 54105947HCID 54105947, compound

Product 1

HCID 68859476HCID 68859476, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of 5.0 g (16.3 mmol) of 5-[(3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine in 55 mL of dimethylformamide cooled to 5° C., was added 1.63 g (40.8 mmol) of sodium hydride as a 60% mineral oil suspension. The ice bath was removed, and the reaction was stirred for 1 hour. To the reaction was then added 7.94 g (48.9 mmol) of 1,1′-carbonyldiimidazole. After stirring the mixture a further 2.5 hours, the mixture was concentrated in vacuo. The residue was partitioned between dichloromethane and a saturated solution of ammonium chloride. The dichloromethane layer was washed twice with each of saturated ammonium chloride, water, and a saturated solution of sodium chloride. The dichloromethane solution was dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with chloroform/methanol (10:0.25 v/v), to give 3.24 g (60%) of the title compound.

Workup

  1. customThe ice bath was removed
  2. stirringAfter stirring the mixture a further 2.5 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was partitioned between dichloromethane
  5. washThe dichloromethane layer was washed twice with each of saturated ammonium chloride, water
  6. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel
  9. washeluting with chloroform/methanol (10:0.25 v/v)

Sources & evidence

ORD record
ord-1ddce3a4f54045e88204069bd9a4fed3
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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