Hydrogen Peroxide → HCID 58075425, compound

HRID 2370225Notes

Reaction equation

HRID 2370225 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:17]([CH3:19])[CH3:18])[C:5]2[CH2:10][CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[OH2:20].OO.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([N:17]([CH3:19])[CH3:18])[C:5]2[CH2:10][C@H:9]([OH:20])[C@@H:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 58414465HCID 58414465, compound

Product 1

HCID 58075425HCID 58075425, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-N,N-dimethyl-7-phenyl-5H-cyclopenta[d]pyrimidin-4-amine (113 mg) in THF (2 mL) at rt was added borane dimethyl sulfide complex in THF (2.0 M solution, 0.41 mL), and the reaction mixture was stirred at rt for 5 h. Water (0.50 mL) was added carefully, followed by 30% H2O2 (0.50 mL) and 1 N NaOH (1 mL). 5 mL EtOAc was added, and the reaction mixture was stirred at rt for 12 h. The crude product was purified by prep. TLC eluting with 50% EtOAc/Hexanes to give the title compound as a yellowish solid (44 mg). LC-MS (M−H2O+H)+=290.05.

Workup

  1. stirringthe reaction mixture was stirred at rt for 12 h
  2. customThe crude product was purified by prep
  3. washTLC eluting with 50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-11b10092ceeb4eecab87c7acd6a08125
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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