m-Chloroperbenzoic acid → N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 536367Notes

Reaction equation

HRID 536367 reaction equation
Cl[C:2]1[C:3]([NH:29][C:30]2[CH:34]=[C:33]([CH3:35])[NH:32][N:31]=2)=[N:4][C:5]([NH:8]C2C=C(C)C(C3CCN(C4CCSCC4)CC3)=CC=2C)=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:35][C:33]1[NH:32][N:31]=[C:30]([NH:29][C:3]2[CH:2]=[CH:7][N:6]=[C:5]([NH2:8])[N:4]=2)[CH:34]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 446111005-chloro-N2-(2,5-dimethyl-4-(1-(tetrahydro-2H-thiopyran-4-yl)piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Product 1

HCID 66829756N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-chloro-N2-(2,5-dimethyl-4-(1-(tetrahydro-2H-thiopyran-4-yl)piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (18 mg, 0.035 mmol) in CH2Cl2 (1 mL) was added m-CPBA (16 mg, 0.71 mmol) at 0° C. The mixture was then warmed up to room temperature and stirred for 30 min; saturated aqueous NaHCO3 solution (3 mL) was then added and the crude product extracted with CH2Cl2 (3×3 mL). The combined organic layers were concentrated and purified by preparative thin layer chromatography (silica gel, 12% MeOH/CH2Cl2 with NH3) to provide 5-chloro-N2-(2,5-dimethyl-4-(1-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl))piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine. ESMS m/z 544.2 (M+H+).

Workup

  1. extractionthe crude product extracted with CH2Cl2 (3×3 mL)
  2. concentrationThe combined organic layers were concentrated
  3. custompurified by preparative thin layer chromatography (silica gel, 12% MeOH/CH2Cl2 with NH3)

Sources & evidence

ORD record
ord-4d774e9d078749edb22f90c7ecca5519
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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