Tetrahydrofuran → HCID 23081948, compound

HRID 1792082Notes

Reaction equation

HRID 1792082 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].C([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]=3C=O)[C:27]3[C:26](=[O:37])[N:25]([CH2:38][O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[C:24](=[O:46])[N:23]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C:22]=3[N:21]=2)[CH2:16][CH2:15]1)=O)(C)(C)C.O1CC[CH2:57][CH2:56]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:2]([O:4][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:56]=[CH2:57])[C:27]3[C:26](=[O:37])[N:25]([CH2:38][O:39][C:40](=[O:45])[C:41]([CH3:43])([CH3:42])[CH3:44])[C:24](=[O:46])[N:23]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:52])([CH3:53])[CH3:51])[C:22]=3[N:21]=2)[CH2:16][CH2:15]1)=[O:11])([CH3:5])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23536931HCID 23536931, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23081948HCID 23081948, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyltriphenylphosphonium bromide (3.52 g) was dissolved in tetrahydrofuran (20 ml), potassium tert-butoxide (948 mg) was added to the solution, and the mixture was stirred at room temperature for 1 hour. A solution of 4-[1,3-bis(2,2-dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (1.94 g) in tetrahydrofuran (20 ml) was added to the obtained reaction mixture at room temperature, and the mixture was stirred at room temperature for 3 hours and 50 minutes. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 704 mg of the title compound from the elution fraction of hexane-ethyl acetate (2:1).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours and 50 minutes
  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
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43a4a930cbcd4fe4bd46bc76aade3211
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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