m-Chloroperbenzoic acid → HCID 178504619, compound

HRID 1809685Notes

Reaction equation

HRID 1809685 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]2[N:31]=[C:30]3[NH:32][N:33]=[C:34]([C:35]4[CH:40]=[CH:39][N:38]=[C:37]([S:41][CH3:42])[N:36]=4)[C:29]3=[CH:28][N:27]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl.CO>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]2[N:31]=[C:30]3[NH:32][N:33]=[C:34]([C:35]4[CH:40]=[CH:39][N:38]=[C:37]([S:41]([CH3:42])=[O:9])[N:36]=4)[C:29]3=[CH:28][N:27]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1785034324-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178504619HCID 178504619, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

m-CPBA (428 mg, 2.4 mmol) was added slowly to a solution of 4-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (from Example 12 supra) (550 mg, 1.2 mmol) in a mixture of dichloromethane and methanol (100 mL, 1:1). The reaction mixture was stirred at room temperature for 20 minutes. The solvent was then removed under reduced pressure and the solid was purified by column chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1) to afford 4-[3-(2-methanesulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-piperidine-1-carboxylic acid tert-butyl ester. (Yield 180 mg, 31.5%).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe solid was purified by column chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1)

Sources & evidence

ORD record
ord-941d1290bef540d3aaab4d1afe2fdc6c
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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