3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentan-1-ol → 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclopentan-1-one

HRID 51511Notes

Reaction equation

HRID 51511 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1>[O-2].[O-2].[Mn+4].ClCCl>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][N:8]([CH:24]3[CH2:28][CH2:27][C:26](=[O:29])[CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 227362353-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentan-1-ol

Product 1

HCID 227362153-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclopentan-1-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclopentan-1-ol (100 mg), activated manganese dioxide (500 mg) and dichloromethane (100 ml) was stirred at ambient temperature for 18 hours to give, after filtration, a solution of 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclopentan-1-one in dichloromethane which was used in the next Example.

Workup

  1. customto give
  2. filtrationafter filtration

Sources & evidence

ORD record
ord-8e306015d83b4af78395e205ccac173e
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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