2-(Tributylstannyl)pyrimidine → 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-(5-pyrimidiny)pyridine

HRID 365893Notes

Reaction equation

HRID 365893 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][CH:18]=[C:19](Br)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([Sn](CCCC)(CCCC)[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=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][CH:18]=[C:19]([C:30]2[CH:29]=[N:28][CH:27]=[N:32][CH:31]=2)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 15480235(S)-2-((5-Bromopyridin-3-yloxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 229618323-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-(5-pyrimidiny)pyridineYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (670 mg, 1.88 mmol) in toluene (10 mL) was added tetrekis(triphenylphosphine)palladium (70 mg, 1%) and tributyl(pyrimidinyl)tin (0.84 g, 2.26 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 (473 mg, 71%): 1H NMR (CDCl3, 300 MHz) δ 1.44 (s, 9H), 1.88-2.00 (m, 2H), 2.05 (m, 1H), 3.30-3.48 (m, 2H), 4.04 (m, 1H), 4.10-4.22 (m, 2H), 4.30 (m, H), 7.64 (s, 1H), 8.42 (d, 1H, J=2.5 Hz), 8.45 (s, 1H), 8.98 (br s, 1H), 9.01 (s, 1H), 9.27 (s, 1H); MS (CI/NH3) m/z 357 (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-7ebdd2f778aa41a9be2171cd4fcd6330
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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