4-[7-(2-Butynyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester → 7-(2-Butynyl)-1,3-dimethyl-8-(piperazin-1-yl)-3,7-dihydropurine-2,6-dione

HRID 1792004Notes

Reaction equation

HRID 1792004 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([CH2:23][C:24]#[C:25][CH3:26])[C:21]3[C:20](=[O:27])[N:19]([CH3:28])[C:18](=[O:29])[N:17]([CH3:30])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:23]([N:22]1[C:21]2[C:20](=[O:27])[N:19]([CH3:28])[C:18](=[O:29])[N:17]([CH3:30])[C:16]=2[N:15]=[C:14]1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:24]#[C:25][CH3:26]

Participants

3

Reactant 1

HCID 230819234-[7-(2-Butynyl)-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 102864607-(2-Butynyl)-1,3-dimethyl-8-(piperazin-1-yl)-3,7-dihydropurine-2,6-dioneYield 84.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-[7-(2-Butynyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (2.5 g) was dissolved in trifluoroacetic acid (15 ml), and the solution was stirred at room temperature for 30 minutes. After removing the solvent by distillation at reduced pressure, the residue was purified by column chromatography using NH-silica gel (silica gel, which surface was treated with amino group: NH-DM2035 manufactured by Fuji Silysia Chemical Ltd.) to obtain 1.6 g of the title compound from a fraction eluted with ethyl acetate.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation at reduced pressure
  3. customthe residue was purified by column chromatography
  4. additionwas treated with amino group

Sources & evidence

ORD record
ord-3f81057871ff4374953b46e6470ebbd7
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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