Potassium Iodide → HCID 86677701, compound

HRID 1499769Notes

Reaction equation

HRID 1499769 reaction equation
[Cl:1][C:2]1[C:3]([CH3:19])=[C:4]([C:10]([O:16][CH2:17][CH3:18])=[C:11]([CH:13](Cl)[CH3:14])[CH:12]=1)[C:5]([NH:7][CH2:8][CH3:9])=[O:6].[I:20][C:21]1[C:29]2[C:24](=[N:25][CH:26]=[N:27][C:28]=2[NH2:30])[NH:23][N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C)C=O.CCOCC>[NH2:30][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[N:23]([CH:13]([C:11]3[C:10]([O:16][CH2:17][CH3:18])=[C:4]([C:3]([CH3:19])=[C:2]([Cl:1])[CH:12]=3)[C:5]([NH:7][CH2:8][CH3:9])=[O:6])[CH3:14])[N:22]=[C:21]([I:20])[C:29]=12

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 86677700HCID 86677700, compoundHCID 178508725HCID 178508725, compound

Product 1

HCID 86677701HCID 86677701, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-chloro-5-(1-chloroethyl)-6-ethoxy-N-ethyl-2-methylbenzamide (130 mg, 0.43 mmol), 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (120 mg, 0.47 mmol), cesium carbonate (210 mg, 0.64 mmol) and potassium iodide (7.1 mg, 0.043 mmol) in N,N-dimethylformamide (1 mL) was heated at 140° C. for 1 h. The mixture was diluted with ether, washed with water, and concentrated. The residue was purified on silica gel (eluting with 0 to 100% EtOAc in hexanes) to give the desired product (0.14 g, 62%). LCMS calculated for C19H23ClIN6O2 (M+H)+: m/z=529.1; Found: 528.9.

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. customThe residue was purified on silica gel (eluting with 0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1423694118e547fd879b2c599349a84a
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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