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Hydrogen Peroxide → 4-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxamide

HRID 2280834
Notes
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Reaction equation

HRID 2280834 reaction equation
[C:1]12([NH:6][C:7]3[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.[OH:17]O.[OH-].[Na+]>CS(C)=O>[C:1]12([NH:6][C:7]3[C:12]([C:13]([NH2:14])=[O:17])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=3)[CH2:2][CH:3]([CH2:5]1)[CH2:4]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 709824294-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 709820104-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl Sulfoxide
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)-pyrimidine-5-carbonitrile (3.45 g, 14.9 mmol) in DMSO (15 mL) was added aqueous hydrogen peroxide solution (8.4 g, 30%, 74.5 mmol) and aqueous sodium hydroxide solution (12.4 mL, 6 mol/L, 74.5 mmol) at 0° C. The mixture was stirred at 50° C. for 15 min and then quenched by the addition of water (30 mL). The solid formed was collected and dried under vacuum to give the desired product (3.5 g, 14.0 mmol, 94% yield). MS (ESI)/m/z=251.2 [M+1]+.

Workup

  1. customquenched by the addition of water (30 mL)
  2. customThe solid formed
  3. customwas collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-37a36fa2b22a4ac9ad0ecc8d9e4a9214
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139534B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes