Trifluoroacetic acid → 7-Allyl-1,3-dimethyl-8-(piperazin-1-yl)-3,7-dihydropurine-2,6-dione

HRID 1792000Notes

Reaction equation

HRID 1792000 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([CH2:23][CH:24]=[CH2:25])[C:21]3[C:20](=[O:26])[N:19]([CH3:27])[C:18](=[O:28])[N:17]([CH3:29])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:23]([N:22]1[C:21]2[C:20](=[O:26])[N:19]([CH3:27])[C:18](=[O:28])[N:17]([CH3:29])[C:16]=2[N:15]=[C:14]1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:24]=[CH2:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 235369534-(7-Allyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 220299677-Allyl-1,3-dimethyl-8-(piperazin-1-yl)-3,7-dihydropurine-2,6-dioneYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(7-allyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)piperazine-1-carboxylic acid tert-butyl ester (1.5 g), trifluoroacetic acid (3 ml), and dichloromethane (10 ml) was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. Water (10 ml) and 5 M potassium carbonate aqueous solution (5 ml) were added to the residue, extracted with dichloromethane, then the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 750 mg of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionWater (10 ml) and 5 M potassium carbonate aqueous solution (5 ml) were added to the residue
  3. extractionextracted with dichloromethane
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dd12a9129b4f4a8e9d7fbb561dade17d
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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