Sodium hydride → HCID 22029940, compound

HRID 1792038Notes

Reaction equation

HRID 1792038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:15](=[O:17])[N:14](COC(=O)C(C)(C)C)[C:13](=[O:26])[N:12]([CH3:27])[C:11]=2[N:10]=[CH:9]1.[H-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:26])[N:12]([CH3:27])[C:11]=2[N:10]=[CH:9]1

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 23081906HCID 23081906, compound

Product 1

HCID 22029940HCID 22029940, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethyl-propionic acid 7-(2-chlorophenyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydropurin-1-ylmethyl ester (144 mg) was dissolved in methanol (2 ml) and tetrahydrofuran (1 ml), and sodium hydride (20 mg) was added thereto. The reaction solution was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with ethyl acetate-diethyl ether to give 72 mg of 7-(2-chlorophenyl)-3-methyl-3,7-dihydropurine-2,6-dione. This was dissolved in N,N-dimethylformamide (1 ml), and N-chlorosuccinimide (35 mg) was added thereto. The reaction solution was stirred at room temperature overnight, diluted with ethyl acetate, and washed with 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 58 mg of the title compound.

Workup

  1. washwashed with 1 N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was triturated with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-545a3981570c46229004ae735ad19ac8
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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