m-Chloroperbenzoic acid → 5-chloro-3-(5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

HRID 539926Notes

Reaction equation

HRID 539926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([S:17][CH3:18])[C:14]([F:19])=[CH:13][N:12]=3)=[N:9][N:8]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:5]2=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:47])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([S:17]([CH3:18])=[O:47])[C:14]([F:19])=[CH:13][N:12]=3)=[N:9][N:8]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 679766315-chloro-3-(5-fluoro-4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 679768755-chloro-3-(5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-chloro-3-(5-fluoro-4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine, 50, (0.078 g, 0.150 mmol) in CH2Cl2 at 0° C. was added mCPBA (0.036 g, 0.160 mmol). The mixture was kept at 0° C. for 2 hr. Then, the mixture was diluted with CH2Cl2, washed with K2CO3 (2×), dried over Na2SO4, filtered and concentrated in vacuo to provide 78 mg of the desired crude which was carried forward without further purification: LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=1.62 min (M+H) 554.47.

Workup

  1. washwashed with K2CO3 (2×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide 78 mg of the desired crude which
  6. customwas carried forward without further purification
  7. customLC/MS Gradient 10-90%, 0.1% formic 5 min

Sources & evidence

ORD record
ord-9aeb502d85b74245862b65b92452a30b
Source dataset
uspto-grants-2014_10
Patent number
US08871774B2

Reaction notes

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