Water → HCID 90408466, compound

HRID 588556Notes

Reaction equation

HRID 588556 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[N:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22])[C:6]([CH2:12]Cl)=[N:7]2.[I:26][C:27]1[C:35]2[C:30](=[N:31][CH:32]=[N:33][C:34]=2[NH2:36])[NH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[NH2:36][C:34]1[N:33]=[CH:32][N:31]=[C:30]2[N:29]([CH2:12][C:6]3[N:5]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:21]([F:24])([F:23])[F:22])[C:4](=[O:25])[C:3]4[C:8](=[CH:9][CH:10]=[CH:11][C:2]=4[Br:1])[N:7]=3)[N:28]=[C:27]([I:26])[C:35]=12

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 90408621HCID 90408621, compoundHCID 178508725HCID 178508725, compound

Product 1

HCID 90408466HCID 90408466, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the quinazolinone, obtained as described above, (100 g, 90% pure, 210 mmol) and 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (50.4 g, 193 mmol) in DMF (600 mL) at RT was added potassium carbonate (80.0 g, 580 mmol) and after 18 hr the reaction mixture was poured into water (1.2 L). The resulting precipitate was collected by filtration, and was washed sequentially with water (500 mL), with EtOAc (600 mL) and finally with Et2O (400 mL). The resulting cake was dried in vacuo to afford the title compound, Intermediate A, as an off white solid (115 g, 89%); Rt 2.28 min, m/z 656/658 (M+H)+ (ES+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwas washed sequentially with water (500 mL), with EtOAc (600 mL) and finally with Et2O (400 mL)
  3. customThe resulting cake was dried in vacuo

Sources & evidence

ORD record
ord-6b312c1260fb4b53b4a6cb28247b322f
Source dataset
uspto-grants-2016_01
Patent number
US09227977B2

Reaction notes

Loading…