Hydrochloric Acid → HCID 23081936, compound

HRID 1792042Notes

Reaction equation

HRID 1792042 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]=[CH2:30])[C:21]3[C:20](=[O:31])[N:19](COC(=O)C(C)(C)C)[C:18](=[O:40])[N:17]([CH3:41])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]=[CH2:30])[C:21]3[C:20](=[O:31])[NH:19][C:18](=[O:40])[N:17]([CH3:41])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23536932HCID 23536932, compound

Product 1

HCID 23081936HCID 23081936, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[1-(2,2-Dimethylpropionyloxymethyl)-7-(2-vinylphenyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (187 mg) was dissolved in methanol (3 ml), and sodium hydride (14 mg) was added thereto. The reaction solution was stirred at room temperature overnight, then neutralized with 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation. The residue was purified by silica gel chromatography to obtain 108 mg of 4-[3-methyl-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester from a fraction eluted with hexane-ethyl acetate (3:2). This was dissolved in trifluoroacetic acid (2 ml), and the solution was concentrated. The residue was purified by NH-silica gel to obtain 84 mg of the title compound from a fraction eluted with ethyl acetate-methanol (15:1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by distillation
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6638aa8a8c584c4eb7e91dcb0fd47e00
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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