Hydrochloric Acid → HCID 23081922, compound

HRID 1792048Notes

Reaction equation

HRID 1792048 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[Cl:29])[C:21]3[C:20](=[O:30])[N:19](COC(=O)C(C)(C)C)[C:18](=[O:39])[N:17]([CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl>O1CCCC1.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[Cl:29])[C:21]3[C:20](=[O:30])[NH:19][C:18](=[O:39])[N:17]([CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23536933HCID 23536933, compound

Product 1

HCID 23081922HCID 23081922, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[7-(2-Chlorophenyl)-1-(2,2-dimethylpropionyloxymethyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (139 mg) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and sodium hydride (10 mg) was added to the solution. Then, the mixture was stirred at room temperature for 1 hour. The mixture was neutralized by adding 1N Hydrochloric acid, and was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation to give 100 mg of 4-[7-(2-chlorophenyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester. This compound was dissolved in N,N-dimethylformamide (2 ml) and potassium carbonate (20 mg) and methyl iodide (0.02 ml) were added to the solution. The mixture was stirred at room temperature for 3 days. The mixture was diluted with ethyl acetate, and washed with water and 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation to give 108 mg of the title compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-87358a15c1744a2588d9a9fcb071b59b
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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