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 524555Notes

Reaction equation

HRID 524555 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)-oneYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5-bromo-3-(2-chlorobenzyl)-2-(chloromethyl)quinazolin-4(3H)-one, (2), (13.6 g, 30.7 mmol) and 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3) (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, (4), as a colourless solid (18.0 g, 94%); Rt 2.17 min; 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-76fa0f4705c944159df5271ef0c4d949
Source dataset
uspto-grants-2016_05
Patent number
US09340545B2

Reaction notes

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