2-(Tributylstannyl)pyrimidine → 3-(1-Boc-2-(s)-azetidinylmethoxy)-5-(5-pyrimidinyl)pyridine

HRID 365889Notes

Reaction equation

HRID 365889 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18](Br)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([Sn](CCCC)(CCCC)[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1)CCC>C1(C)C=CC=CC=1>[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:29]2[CH:28]=[N:27][CH:26]=[N:31][CH:30]=2)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 10688713(S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

Product 1

HCID 229618163-(1-Boc-2-(s)-azetidinylmethoxy)-5-(5-pyrimidinyl)pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromopyridine (580 mg, 1.69 mmol) in toluene (10 mL) was added tetrekis(triphenylphosphine)palladium (58 mg, 1%) and tributyl(pyrimidinyl)tin (0.75 g, 2.03 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 2:3) to afford an oil (450 mg, 78%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 2.30-2.44 (m, 2H), 3.88-3.96 (m, 2H), 4.22 (m, 1H), 4.44 (m, 1H), 4.58 (m, 1H), 7.44 (m, 1H), 8.44 (m, 2H), 8.98 (s, 2H); MS (CI/NH3) m/z 343 (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 2:3)

Sources & evidence

ORD record
ord-6117dd7639be4772a4dee0d03bc177ef
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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