Dimethylformamide → HCID 68007443, compound

HRID 1027788Notes

Reaction equation

HRID 1027788 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[NH:9][C:8]2[C:3]1=[N:4][C:5](/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:6][CH:7]=2.N12CCN(CC1)CC2.CN(C)C=O.[N:33]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1>O>[CH3:1][N:2]1[C:10](=[O:11])[N:9]([C:38]([N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:39])[C:8]2[C:3]1=[N:4][C:5](/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:6][CH:7]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9237DabcoHCID 709371-Pyrrolidinecarbonyl chlorideHCID 68007553HCID 68007553, compound

Product 1

HCID 68007443HCID 68007443, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 9-methyl-2-[(E)-2-phenylethenyl]-7,9-dihydro-8H-purine-8-one <the compound of Reference Example 3> (100 mg), 1,4-diazabicyclo[2.2.2]octane (133 mg) and N,N-dimethylformamide (3 ml) was added dropwise 1-pyrrolidinecarbonyl chloride (106 mg) at room temperature and the mixture was stirred for 1 hour. To the reaction mixture was added water (50 ml) and the mixture was extracted with ethyl acetate (80 ml×2). The organic layer was dried over anhydrous magnesium sulfate and was filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜0/100) to give the title compound 56 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (80 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜0/100)

Sources & evidence

ORD record
ord-f998d141ff4e4715ab7fe161fa5292bc
Source dataset
uspto-grants-2014_05
Patent number
US08735406B2

Reaction notes

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