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Potassium Carbonate → 7-isobutyl-5-methyl-3-(phenylamino)-2-(3-phenylprop-2-ynyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81414
Notes
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Reaction equation

HRID 81414 reaction equation
[CH2:1]([N:5]1[C:10]2=[N:11][NH:12][C:13]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:9]2[C:8](=[O:21])[N:7]([CH3:22])[C:6]1=[O:23])[CH:2]([CH3:4])[CH3:3].Br[CH2:25][C:26]#[C:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:25][C:26]#[C:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:13]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:9]2[C:8](=[O:21])[N:7]([CH3:22])[C:6]1=[O:23])[CH:2]([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10987157(3-Bromoprop-1-yn-1-yl)benzeneHCID 251780697-Isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 426425807-isobutyl-5-methyl-3-(phenylamino)-2-(3-phenylprop-2-ynyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 7-isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (48.6 mg, 0.155 mmol), (3-bromoprop-1-ynyl)benzene (60.5 mg, 0.31 mmol) and potassium carbonate (42.8 mg, 0.31 mmol) in DMF (1.5 mL) is stirred at room temperature overnight. The mixture is filtered through a 0.45 μm microfilter and the filtrate is purified by a semi-preparative HPLC to give pure product as white solids. MS (ESI) m/z 428.2 [M+H]+.

Workup

  1. filtrationThe mixture is filtered through a 0.45 μm microfilter
  2. customthe filtrate is purified by a semi-preparative HPLC
  3. customto give pure product as white solids

Sources & evidence

ORD record
ord-b4648b677668482cadba282d70a29876
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846693B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes