Sodium hydride → HCID 23081920, compound

HRID 1792085Notes

Reaction equation

HRID 1792085 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]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>O1CCCC1.CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][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]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:16]=3[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 235369604-[1-(2,2-Dimethylpropionyloxymethyl)-3-ethoxycarbonylmethyl-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23081920HCID 23081920, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[1-(2,2-Dimethylpropionyloxymethyl)-3-ethoxycarbonylmethyl-2,6-dioxo-7-(2-vinylphenyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (89 mg) was dissolved in tetrahydrofuran (1 ml) and methanol (2 ml), sodium hydride (7 mg) was added to the solution, and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and filtered, followed by concentration of the filtrate under reduced pressure. The residue was purified by silica gel column chromatography to give 60 mg of the title compound from the elution fraction of hexane-ethyl acetate (1:2).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea04dafa420d4f0d9abd859d79b64910
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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