2-(Tributylstannyl)pyrimidine → HCID 22961813, compound

HRID 2305177Notes

Reaction equation

HRID 2305177 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:22])=[C:19](Br)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([Sn](CCCC)(CCCC)[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)CCC>C1(C)C=CC=CC=1>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:22])=[C:19]([C:31]2[CH:30]=[N:29][CH:28]=[N:33][CH:32]=2)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 22872666HCID 22872666, compound

Product 1

HCID 22961813HCID 22961813, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-bromo-6-chloropyridine (400 mg, 1.1 mmol) in toluene (10 mL) was added tetrekis(triphenylphosphine)palladium (40 mg, 1%) and tributyl(pyrimidinyl)tin (0.51 g, 1.38 mmol). The mixture was stirred and heated under reflux for 16 h. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtOAc, 10:1 to 2:1) to afford an oil (335 mg, 80%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 1.85-2.00 (m, 2H), 2.00-2.10 (m, 2H), 3.38 (m, 1H), 4.00 (m 1H), 4.14 (m, 1H), 4.24 (m, 1H), 7.40 (s, 1H), 8.20 (d, 1H, J=3.0 Hz), 8.88 (s, 2H), 9.28 (s, 1H); MS (CI/NH3) m/z 277 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. customSolvent was evaporated
  4. customthe residue was chromatographed (silica gel; hexane/EtOAc, 10:1 to 2:1)

Sources & evidence

ORD record
ord-2ee95c2404b34bf0a58020f2319393f5
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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