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Hydrogen Peroxide → 2-((6-(1-Methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzamide

HRID 594960
Notes
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Reaction equation

HRID 594960 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[C:20]#[N:21])[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.[OH-:26].[Na+].OO>O.C(O)C.CCOC(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[C:20]([NH2:21])=[O:26])[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 671122832-((6-(1-Methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzonitrile

Product 1

HCID 529143862-((6-(1-Methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2-((6-(1-methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzonitrile (see Example 1) (40 mg, 0.24 mmol), sodium hydroxide (0.5 mL, 1M in H2O) and hydrogen peroxide (0.2 mL of a 33% solution in water) in ethanol (5 mL) was heated at 60° C. for 3 h. After cooling to rt the mixture was diluted with EtOAc and washed with water. The organic phase was collected, dried (MgSO4) and concentrated in vacuo to give the title product. 1H NMR (d6-DMSO) δ 9.95 (s, 1H), 8.99 (s, 1H), 8.10-8.16 (m, 3H), 7.66 (s, 1H), 7.60 (dd, 1H), 7.54 (s, 1H), 7.37-7.40 (m, 2H), 6.95 (br s, 1H), 5.85 (s, 2H), 3.88 (s, 3H); LC-MS method B, (ES+) 349.1, RT=6.46 min.

Workup

  1. temperatureAfter cooling to rt the mixture
  2. washwashed with water
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2860604da1c145b78ceb00c09c6adf08
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242987B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes