Hydrochloric Acid → (E)-5-(1-(4-fluorophenyl)prop-1-enyl)-2-(piperazin-1-yl)pyrimidine

HRID 1498846Notes

Reaction equation

HRID 1498846 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:16][CH:17]=2)(O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:13]=[N:14][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:16][CH:17]=2)=[CH:9]\[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118023301HCID 118023301, compound

Product 1

HCID 118023005(E)-5-(1-(4-fluorophenyl)prop-1-enyl)-2-(piperazin-1-yl)pyrimidineYield 103.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-(4-fluorophenyl)-1-(2-(piperazin-1-yl)pyrimidin-5-yl)propan-1-ol (200 mg, 0.6 mmol) in dioxane (10 mL) was added HCl in dioxane (4 M, 10 mL), and the reaction was stirred at RT for 1 h. LCMS showed the reaction was completed. The mixture was concentrated to an oil, which was purified by Combiflash with dichloromethane:methanol=20:1 to give the title compound as a light yellow solid (185 mg, 98%). MS (ES+) C17H19FN4 requires: 298. found: 299 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to an oil, which
  2. customwas purified by Combiflash with dichloromethane

Sources & evidence

ORD record
ord-79d8037ffd1240abad6d3544085f95e6
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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