Acetic Anhydride → 3-[6-[4-(6-Amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

HRID 1024621Notes

Reaction equation

HRID 1024621 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2C(=O)C3[CH:15]=[N:16][N:17]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]#[N:22])[C:11]=3[N:10]=[C:9]2[C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)=[CH:4][CH:3]=1.[C:41]([O-:44])(=O)[CH3:42].[Na+].C(O[C:50](=O)[CH3:51])(=O)C>>[NH2:10][C:9]1[N:8]=[CH:51][C:50]([C:29]2[CH:30]=[CH:31][C:26]([C:9]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[C:41](=[O:44])[C:42]4[CH:15]=[N:16][N:17]([C:18]5[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=5)[C:21]#[N:22])[C:11]=4[N:10]=3)=[CH:27][CH:28]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 578994373-{5-(4-Chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl}-benzonitrile

Product 1

HCID 578994223-[6-[4-(6-Amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

Procedure

A solution of 2-(4-bromo-phenyl)-1-(4-chloro-phenyl)-9-(3-methanesulfinyl-phenyl)-1,9-dihydro-purin-6-one (2, 2.60 g, 4.81 mmol) in acetic anhydride (22 mL), sodium acetate (1.48 g, 18.0 mmol) is added and the resulting mixture is then heated at reflux for 4 h. The reaction mixture is concentrated to a dry residue. It is taken in ethyl acetate and washed successively with 10% sodium bicarbonate solution and brine, dried over Na2SO4, concentrated, and purified by column chromatography to provide (3-(2-(4-bromophenyl)-1-(4-chlorophenyl)-6-oxo-1H-purin-9(6H)-yl)phenylthio)methyl acetate (3).

Workup

  1. temperaturethe resulting mixture is then heated
  2. temperatureat reflux for 4 h
  3. concentrationThe reaction mixture is concentrated to a dry residue
  4. washwashed successively with 10% sodium bicarbonate solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-dd7cf76abf4b44eaa4a8c8774a7258ba
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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