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Potassium Carbonate → 4-[7-(2-Butynyl)-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1792069
Notes
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Reaction equation

HRID 1792069 reaction equation
[C:1]([O:5][C:6]([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])[NH:17][C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:35]([O:41][CH2:42]Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][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]([CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[C:16]=3[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 235369444-[7-(2-Butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 230819184-[7-(2-Butynyl)-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

4-[7-(2-Butynyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (1.1 g) and potassium carbonate (0.43 g) were dissolved in N,N-dimethylformamide (15 ml), and chloromethyl pivalate (0.60 ml) was added to the solution while cooling on ice. After the mixture was stirred at room temperature overnight, the reaction mixture was diluted with ethyl acetate and washed with water. Insoluble white solid was collected by filtration, and washed with a mixture of hexane-ethyl acetate (1:1) to give 0.57 g of the title compound.

Workup

  1. temperaturewhile cooling on ice
  2. washwashed with water
  3. filtrationInsoluble white solid was collected by filtration
  4. washwashed with a mixture of hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bb1d316206cb4395ac0d259040c7c242
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074798B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes