2-(Tributylstannyl)pyrimidine → 3-(1-Boc-2-(s)-azetidinylmethoxy)-6-chloro-5-(5-pyrimidinyl)pyridine

HRID 365891Notes

Reaction equation

HRID 365891 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][C:17]([Cl:21])=[C:18](Br)[CH:19]=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[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][C:17]([Cl:21])=[C:18]([C:30]2[CH:29]=[N:28][CH:27]=[N:32][CH:31]=2)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 228726673-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine

Product 1

HCID 229618213-(1-Boc-2-(s)-azetidinylmethoxy)-6-chloro-5-(5-pyrimidinyl)pyridineYield 120.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine (500 mg, 1.1 mmol) in toluene (10 mL) was added tetrekis(triphenylphosphine)palladium (50 mg, 1%) and tributyl(pyrimidinyl)tin (0.64 g, 1.72 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 (500 mg, 100%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 2.26-2.42 (m, 2H), 3.84-3.92 (m, 2H), 4.20 (m, 1H), 4.40 (m, 1H), 4.54 (m, 1H), 7.31 (d, 1H, J=3.0 Hz), 8.22 (d, 1H, J=3.0 Hz), 8.88 (s, 2H), 9.28 (s, 1H); MS (CI/NH3) m/z 377 (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-8e2f523b38084bd49247329bc776f7a6
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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