2-(Tributylstannyl)pyrimidine → HCID 22961903, compound

HRID 365903Notes

Reaction equation

HRID 365903 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:5]=[N:6][C:7]=1[Cl:8].C([Sn](CCCC)(CCCC)[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1)CCC>C1(C)C=CC=CC=1>[Cl:8][C:7]1[N:6]=[CH:5][C:4]([O:9][CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])=[CH:3][C:2]=1[C:25]1[CH:24]=[N:23][CH:22]=[N:27][CH:26]=1

Participants

4

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 9901120HCID 9901120, compound

Product 1

HCID 22961903HCID 22961903, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 5-bromo-6-chloro-3-(1-methyl-2-(R)-pyrrolidinylmethoxy)-pyridine (390 mg, 1.27 mmol) in toluene (15 mL) was added tetrekis(triphenylphosphine)palladium (40 mg, 1%) and tributyl(pyrimidinyl)tin (0.57 g, 1.53 mmol). The mixture was stirred and heated under reflux for 6 h. Solvent was evaporated and the residue was chromatographed (silica gel; CH2Cl2 /MeOH, 10:0.3 to 10:1) to afford an oil (193 mg, 50%): 1H NMR (CDCl3, 300 MHz) δ 1.62 (m, 1H), 1.68-1.90 (m, 2H), 2.02 (m, 1H), 2.32 (m, 1H), 2.50 (s, 3H), 2.70 (m, 1H), 3.12 (m, 1H), 3.98-4.06 (m, 2H), 7.25 (m, 1H), 8.18 (d, 1H, J=3.0 Hz), 8.87 (s, 2H), 9.29 (s, 1H); MS (CI/NH3) m/z 305 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 h
  3. customSolvent was evaporated
  4. customthe residue was chromatographed (silica gel; CH2Cl2 /MeOH, 10:0.3 to 10:1)

Sources & evidence

ORD record
ord-915f1c758fa8476da3992e251fd4b941
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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