Hydrochloric Acid → (E)-6-(4-chlorostyryl)pyrimidin-4(3H)-one

HRID 2059879Notes

Reaction equation

HRID 2059879 reaction equation
Cl[C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.C(=O)([O-])[O-:26].[K+].[K+].Cl>O1CCOCC1.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10](/[CH:9]=[CH:8]/[C:6]2[N:5]=[CH:4][NH:3][C:2](=[O:26])[CH:7]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 11430Potassium CarbonateHCID 58579925(E)-4-chloro-6-(4-chlorostyryl)pyrimidine

Product 1

HCID 136097744(E)-6-(4-chlorostyryl)pyrimidin-4(3H)-oneYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (E)-4-chloro-6-(4-chlorostyryl)pyrimidine Part A (120 mg, 0.48 mmol), DABCO (107 mg, 0.96 mmol), and potassium carbonate (660 mg, 4.78 mmol) in Dioxane (0.4 mL) and Water (4 mL) was stirred at 60° C. overnight. The reaction was cooled to RT, acidified with 10% HCl, extracted with EtOAC, dried (Na2SO4), and concentrated. The product was triturated with DCM to afford the desired product (E)-6-(4-chlorostyryl)pyrimidin-4(3H)-one 20B (108 mg, 0.46 mmol, 97% yield) as a light yellow solid.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with EtOAC
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product was triturated with DCM

Sources & evidence

ORD record
ord-4a662a175d0e416d90fdf5df6349090d
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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