Potassium Carbonate → 5-((5-Bromopyridin-3-yl)oxy)pyrimidine

HRID 1045813

Reaction equation

HRID 1045813 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](F)[CH:7]=1.[OH:9][C:10]1[CH:11]=[N:12][CH:13]=[N:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Li+].[Cl-]>[Br:1][C:2]1[CH:7]=[C:6]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 565855Pyrimidin-5-olHCID 8202063-Bromo-5-fluoropyridine

Product 1

HCID 510379325-((5-Bromopyridin-3-yl)oxy)pyrimidineYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 433294Lithium ChlorideSolvent

Procedure

A mixture of 3-bromo-5-fluoropyridine (2.0 g, 11 mmol, 1.0 eq), 5-hydroxypyrimidine (1.3 g, 14 mmol, 1.2 eq), and potassium carbonate (2.4 g, 17 mmol, 1.5 eq) in DMF (40 mL) was microwaved at 200° C. for 30 minutes. The reaction was diluted with 3M LiCl and extracted (3×) with CH2Cl2. The combined organics were dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 1.7 g (92%) of the title compound as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 9.07 (s, 1H), 8.77 (s, 2H), 8.58 (d, J=1.8 Hz, 1H), 8.54 (d, J=2.4 Hz, 1H), 8.02 (t, J=2.1 Hz, 1H); ES-MS [M+1]+: 252.0.

Workup

  1. customwas microwaved at 200° C. for 30 minutes
  2. extractionextracted (3×) with CH2Cl2
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a943e5f4e67c4f46878e698fd2bbb906
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Linked notes

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