Tributylvinyltin → HCID 58075410, compound

HRID 2370219Notes

Reaction equation

HRID 2370219 reaction equation
Br[C:2]1[C:3]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[N:4][C:5]([Cl:10])=[N:6][C:7]=1[NH:8][CH3:9].[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:5]1[N:4]=[C:3]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])[C:2]([CH:17]=[CH2:18])=[C:7]([NH:8][CH3:9])[N:6]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 58075473HCID 58075473, compound

Product 1

HCID 58075410HCID 58075410, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5-bromo-2-chloro-N-methoxy-N-methyl-6-(methylamino)pyrimidine-4-carboxamide (100 mg), tributyl(vinyl)stannane (113 mg), tetrakis (23 mg) in toluene (1.6 mL) was heated at 95° C. for 12 h, and the solvent was removed. The residue was purified by preparative TLC eluting with 50% EtOAc/Hexanes to give the title compound as a colorless oil (23 mg). LC-MS (M+H)+=257.06.

Workup

  1. customthe solvent was removed
  2. customThe residue was purified by preparative TLC
  3. washeluting with 50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-515adb24ada24faca88a60caaa6e3fa9
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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