Tributylvinyltin → HCID 11363485, compound

HRID 1912842Notes

Reaction equation

HRID 1912842 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5](I)[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[O:19])=[CH:13][CH:12]=1.[CH:33]([Sn](CCCC)(CCCC)CCCC)=[CH2:34]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH:33]=[CH2:34])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[O:19])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 23155066HCID 23155066, compound

Product 1

HCID 11363485HCID 11363485, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

In 2 mL of dimethylformamide, 158 mg (0.28 mmol) of 1-[4-(6-amino-8-iodopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea was dissolved, and 262 mg (0.82 mmol) of vinyltributyltin and 20 mg (0.01 mmol) of tetrakistriphenylphosphine palladium was added thereto and the mixture solution was stirred at 95° C. for three hours. The reaction solution was concentrated and purified by a silica gel column (dichloromethane:methanol=9:1) to obtain 122 mg (93%) of a target product as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by a silica gel column (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-cdd25d3dd80f42d291d1aa9395d1be36
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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