Trifluoroacetic acid → [7-(2-Butynyl)-2,6-dioxo-8-(piperazin-1-yl)-1,2,6,7-tetrahydropurin-3-yl] acetic acid methyl ester trifluoroacetate

HRID 1792063Notes

Reaction equation

HRID 1792063 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])[NH:19][C:18](=[O:28])[N:17]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[CH3:33][O:32][C:30](=[O:31])[CH2:29][N:17]1[C:16]2[N:15]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:22]([CH2:23][C:24]#[C:25][CH3:26])[C:21]=2[C:20](=[O:27])[NH:19][C:18]1=[O:28]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 235369464-[7-(2-Butynyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69566880[7-(2-Butynyl)-2,6-dioxo-8-(piperazin-1-yl)-1,2,6,7-tetrahydropurin-3-yl] acetic acid methyl ester trifluoroacetate

Procedure

4-[7-(2-Butynyl)-3-methoxycarbonylmethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (13 mg) was dissolved in trifluoroacetic acid (0.5 ml), and the solution was stirred at room temperature for 30 minutes. After the solvent was removed by distillation, a half of the residue was purified by HPLC with a reversed phase system column using water-acetonitrile-trifluoroacetic acid system as elution solvent to give 2.4 mg of the title compound.

Workup

  1. customAfter the solvent was removed by distillation
  2. customa half of the residue was purified by HPLC with a reversed phase system column
  3. washas elution solvent

Sources & evidence

ORD record
ord-d474136064c3418089ffd13c09f942de
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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