Potassium Carbonate → 2-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-5-bromo-3-(2-chloro benzyl)quinazolin-4(3H)-one

HRID 400545Notes

Reaction equation

HRID 400545 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:22])[N:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[C:6]([CH2:12]Cl)=[N:7]2.[I:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[N:30][C:31]=2[NH2:33])[NH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:33][C:31]1[N:30]=[CH:29][N:28]=[C:27]2[N:26]([CH2:12][C:6]3[N:5]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:4](=[O:22])[C:3]4[C:8](=[CH:9][CH:10]=[CH:11][C:2]=4[Br:1])[N:7]=3)[N:25]=[C:24]([I:23])[C:32]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 665792385-bromo-3-(2-chlorobenzyl)-2-(chloromethyl)quinazolin-4(3H)-oneHCID 178508725HCID 178508725, compound

Product 1

HCID 665800572-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-5-bromo-3-(2-chloro benzyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5-bromo-3-(2-chlorobenzyl)-2-(chloromethyl)quinazolin-4(3H)-one, (8), (13.6 g, 30.7 mmol) and 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1) (8.09 g, 30.7 mmol) in DMF (300 mL was added potassium carbonate (6.36 g, 46.0 mmol) and the reaction maintained at RT in the dark for 24 hr. The mixture was poured onto water (4.0 L) and the resulting suspension was stirred at RT for 1 hr. The precipitate was isolated by filtration and dried in vacuo to afford the title compound, Intermediate A, as a colourless solid (18.0 g, 94%); m/z 622/624 [M+H]+ (ES+).

Workup

  1. additionThe mixture was poured onto water (4.0 L)
  2. customThe precipitate was isolated by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-37c731222bb14033bbfe77ae0c4c404f
Source dataset
uspto-grants-2014_06
Patent number
US08741909B2

Reaction notes

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