Acetic Anhydride → (4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylthio)methyl acetate

HRID 1024602Notes

Reaction equation

HRID 1024602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:32])=O)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[C:33]([O:36]C(=O)C)(=[O:35])[CH3:34]>>[C:33]([O:36][CH2:32][S:30][C:27]1[CH:28]=[CH:29][C:24]([C:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=2)=[CH:25][CH:26]=1)(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 578993935-(4-Chloro-phenyl)-6-(4-methanesulfinyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 57899441(4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylthio)methyl acetate

Procedure

To a solution of 5-(4-chloro-phenyl)-6-(4-methanesulfinyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (1.20 g, 2.60 mmol) in dry acetic anhydride (12 mL) sodium acetate (0.800 g, 9.76 mmol) is added and the resulting mixture is heated to reflux. After 5 h, the reaction mixture is concentrated. The crude product is purified by column chromatography (silica gel, 60-120 mesh) to afford (4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylthio)methyl acetate.

Workup

  1. temperaturethe resulting mixture is heated to reflux
  2. concentrationthe reaction mixture is concentrated
  3. customThe crude product is purified by column chromatography (silica gel, 60-120 mesh)

Sources & evidence

ORD record
ord-272f01b8a0e347d5a9bf1289ed357eec
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

Loading…