HCID 23081908, compound → HCID 23081919, compound

HRID 1792027Notes

Reaction equation

HRID 1792027 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH:35]=O)[C:27]3[C:26](=[O:37])[N:25]([CH3:38])[C:24](=[O:39])[N:23]([CH3:40])[C:22]=3[N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH:35]=[CH2:1])[C:27]3[C:26](=[O:37])[N:25]([CH3:38])[C:24](=[O:39])[N:23]([CH3:40])[C:22]=3[N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:9])([CH3:10])[CH3:8]

Participants

6

Reactant 2

HCID 23081908HCID 23081908, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23081919HCID 23081919, compoundYield 200.8%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (9 mg) was dissolved in tetrahydrofuran (1 ml), and methyl triphenyl phosphonium bromide (31 mg) was added thereto. The reaction mixture was stirred at room temperature for 30 minutes, and a solution of 4-[7-(2-formylphenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (20 mg) in tetrahydrofuran (1 ml) was added thereto. The reaction solution was stirred at room temperature for 1 hour, diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 40 mg of 4-[7-(2-vinylphenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester. This product (12 mg) was dissolved in trifluoroacetic acid, and the solution was concentrated. The residue was purified by reversed phase high performance liquid chromatography to give 4.38 mg of the title compound.

Workup

  1. stirringThe reaction solution was stirred at room temperature for 1 hour
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ada8ac12677340b39fd183138d9946c7
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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