m-Chloroperbenzoic acid → HCID 178504618, compound

HRID 1809690Notes

Reaction equation

HRID 1809690 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17](=[O:43])[NH:18][CH: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)([CH3:15])([CH3:14])[CH3:13]>ClCCl.CO>[C:12]([O:16][C:17](=[O:43])[NH:18][CH: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)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178503431HCID 178503431, compound

Product 1

HCID 178504618HCID 178504618, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

m-CPBA (490 mg, 2.41 mmol) was added slowly to a solution of {-4-[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (from Example 18 supra) (550 mg, 1.21 mmol) in a mixture of dichloromethane and methanol (20 mL, 1:1). The reaction mixture was stirred at room temperature for 25 minutes. The solvent was then removed under reduced pressure and the solid was purified by column chromatography (silica gel, 20 g, 200-300 mesh, eluting with dichloromethane:methanol, 5:1) to afford {4-[3-(2-methanesulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 300 mg, 52.9%).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe solid was purified by column chromatography (silica gel, 20 g, 200-300 mesh, eluting with dichloromethane:methanol, 5:1)

Sources & evidence

ORD record
ord-7af9ee44784943ada8d11aa646a45246
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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