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Potassium Carbonate → 7-isobutyl-5-methyl-3-(phenylamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81408
Notes
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Reaction equation

HRID 81408 reaction equation
[CH2:1]([N:5]1[C:10]2[NH:11][N: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]1[CH:31]=[CH:30][C:29]([B:32]2[O:36][C:35]([CH3:38])([CH3:37])[C:34]([CH3:40])([CH3:39])[O:33]2)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([B:32]4[O:33][C:34]([CH3:40])([CH3:39])[C:35]([CH3:38])([CH3:37])[O:36]4)=[CH:30][CH:31]=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 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178448719HCID 178448719, compound

Product 1

HCID 685027217-isobutyl-5-methyl-3-(phenylamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 38%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

A mixture of 7-isobutyl-5-methyl-3-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (12.0 mg, 0.0383 mmol), 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.0383 mmol) and potassium carbonate (5.3 mg, 0.0383 mmol) in acetone (2.5 mL) is stirred at room temperature overnight. The solvent is evaporated under reduced pressure. The residue is directly purified by chromatography to give 7.0 mg product as white solids (Yield: 38.0%). MS (ESI) m/z 530.3 [M+H]+.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customThe residue is directly purified by chromatography

Sources & evidence

ORD record
ord-7b71a89a30b244e3924ac0ed1dfe53a8
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