Sodium hydride → HCID 12004099, compound

HRID 971253Notes

Reaction equation

HRID 971253 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].[H-].[Na+].[Cl:9][C:10]1[C:11]([N:16]2[CH2:25][CH2:24][C:23]3[C:22]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)=[N:21][C:20](S(C)(=O)=O)=[N:19][C:18]=3[CH2:17]2)=[N:12][CH:13]=[CH:14][CH:15]=1>CN(C=O)C>[F:36][C:33]([F:34])([F:35])[C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:22]2[C:23]3[CH2:24][CH2:25][N:16]([C:11]4[C:10]([Cl:9])=[CH:15][CH:14]=[CH:13][N:12]=4)[CH2:17][C:18]=3[N:19]=[C:20]([O:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[N:21]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 12004367HCID 12004367, compound

Product 1

HCID 12004099HCID 12004099, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl glycolate (31 mg, 0.33 mmol) was dissolved in DMF (dry), NaH (8 mg, 0.31 mmol) was added and stirred at room temperature under an atmosphere of Nitrogen for 30 min. 7-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylsulfonyl)pyrido[3,4-d]pyrimidin-4-amine (120.0 mg, 0.22 mol) (in 4 mL DMF, dry) was added to the above mixture. The reaction was heated via microwave at 180° C. for 15 minutes. Solvent was removed and the residue was purified by flash chromatography over silica gel to obtain the product as a white solid (25 mg).

Workup

  1. temperatureThe reaction was heated via microwave at 180° C. for 15 minutes
  2. customSolvent was removed
  3. customthe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-3f3ca6136b8349f4b2e8c004a832eb64
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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