Dimethyl malonate → HCID 178500073, compound

HRID 2354852Notes

Reaction equation

HRID 2354852 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[CH2:12]([N:19]1[C:27]([OH:28])=[N:26][C:25]2[C:20]1=[N:21][C:22]([CH2:30]Cl)=[N:23][C:24]=2[NH2:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:12]([N:19]1[C:27]([OH:28])=[N:26][C:25]2[C:20]1=[N:21][C:22]([CH2:30][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[N:23][C:24]=2[NH2:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 178508406HCID 178508406, compound

Product 1

HCID 178500073HCID 178500073, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To dimethyl malonate (493 mg, 3.73 mmol) in DMF (8 ml) was added in an ice bath sodium hydride (75 mg, 3.13 mmol). Then the mixture was stirred at room temperature for 30 minutes. Thereto was added 9-benzyl-2-chloromethyl-8-hydroxyadenine (0.10 g, 0.37 mmol), and the mixture was stirred at room temperature for 21 hours. After removing the solvent, the residue was poured into water, concentrated, and neutralized with hydrochloric acid. The resulting solid was filtered, washed with water and dried in vacuo under heating to give 9-benzyl-2-(2,2-dimethoxycarbonylethyl)-8-hydroxyadenine (92 mg, 0.24 mmol) as a white solid. Thus obtained 9-benzyl-2-(2,2-dimethoxycarbonylethyl)-8-hydroxyadenine (79 mg, 0.20 mmol) was added to a mixed solvent of concentrated hydrochloric acid (2 ml) and 1,4-dioxane (6 ml), and the mixture was refluxed for 6 hours. After the reaction mixture was neutralized in an ice bath with saturated sodium hydrogencarbonate solution, the resulting solid was filtered, washed with water and dried in vacuo under heating to give the captioned compound (55 mg, 0.18 mmol) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 21 hours
  2. customAfter removing the solvent
  3. additionthe residue was poured into water
  4. concentrationconcentrated
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customdried in vacuo
  8. temperatureunder heating

Sources & evidence

ORD record
ord-faddd1f48d37494b8fe57cbc949a72ef
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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