Dimethylformamide dimethyl acetal → 5-(4-Chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693509Notes

Reaction equation

HRID 1693509 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:12](=[O:25])[C:13]3[CH:18]=[N:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:14]=3[N:15]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:35](OC)[N:36]([CH3:38])[CH3:37]>>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([N:11]2[C:12](=[O:25])[C:13]3[CH:18]=[N:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:14]=3[N:15]=[C:10]2[C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[CH:35][N:36]([CH3:38])[CH3:37])=[CH:9][CH:8]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 116765606-(4-Acetyl-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 672827725-(4-Chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneYield 100%

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(4-acetyl-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (50 mg, 0.11 mmol) and N,N-dimethylformamide dimethyl acetal (1 mL) is heated at 80° C. for 14 h. After cooling down to room temperature, excess N,N-dimethylformamide dimethyl acetal is removed under vacuum to provide 5-(4-chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as yellow solid (56 mg, 100%). HPLC-MS calculated for C28H22ClN5O2 (M+H+): 496.2. Found: 496.2.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customexcess N,N-dimethylformamide dimethyl acetal is removed under vacuum

Sources & evidence

ORD record
ord-a36fc6b686b34d98b14013c38ae62572
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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