Hydrochloric Acid → 5-(pyrimidin-2-yl)pyridin-2(1H)-one

HRID 525405Notes

Reaction equation

HRID 525405 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[O:14]1CCOCC1.Cl>O>[N:9]1[CH:10]=[CH:11][CH:12]=[N:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2](=[O:14])[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 578217612-(6-Fluoropyridin-3-yl)pyrimidine

Product 1

HCID 580164905-(pyrimidin-2-yl)pyridin-2(1H)-oneYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with 2-(6-fluoropyridin-3-yl)pyrimidine (0.150 g, 0.856 mmol), dioxane (3.0 mL), and water (1.00 mL). Concentrated hydrochloric acid (37%)(0.25 mL) was added, the system was flushed with argon, the tube was sealed, and the reaction mixture stirred at 100° C. for 1.5 hours. The reaction mixture was then partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 5-(pyrimidin-2-yl)pyridin-2(1H)-one (0.079 g, 0.456 mmol, 53% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.45 (dd, J=9.59, 0.78 Hz, 1H), 7.33 (t, J=4.89 Hz, 1H), 8.32 (td, J=10.07, 2.35 Hz, 2H), 8.79 (d, J=4.89 Hz, 2H), 11.96 (br. s., 1H). m/z (ESI) 174 (M+H)+.

Workup

  1. customthe system was flushed with argon
  2. customthe tube was sealed
  3. customThe reaction mixture was then partitioned between EtOAc and saturated aqueous NaHCO3 solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1f3bafc158c3497e9bd4626b237f5361
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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