1,4-Dioxane hydrochloride → 2-(4-Fluorophenyl)-2-(2-(piperazin-1-yl)pyrimidin-5-yl)ethanol

HRID 1498859Notes

Reaction equation

HRID 1498859 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[N:15][CH:16]=2)[CH2:9][OH:10])=[CH:4][CH:3]=1.Cl.O1CCOCC1>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:15][CH:16]=2)[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118023051Tert-butyl 4-(5-(1-(4-fluorophenyl)-2-hydroxyethyl)pyrimidin-2-yl)piperazine-1-carboxylat

Product 1

HCID 1180227232-(4-Fluorophenyl)-2-(2-(piperazin-1-yl)pyrimidin-5-yl)ethanolYield 61.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(5-(1-(4-fluorophenyl)-2-hydroxyethyl)pyrimidin-2-yl)piperazine-1-carboxylat (450 mg, 1.08 mmol) in dioxane (5 mL) was added HCl/dioxane (5 mL). The mixture was stirred at RT overnight. LCMS showed the reaction was completed. The solution was concentrated and purified by silica gel chromatography (DCM:CH3OH=10:1) to get the title compound as a yellow solid (0.2 g, 53%). MS (ES+) C16H19FN4O requires: 302. found: 303 [M+H]+.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by silica gel chromatography (DCM:CH3OH=10:1)

Sources & evidence

ORD record
ord-f486ffde226e4f12a44453195fa9241f
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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