4-Cyanopiperidine → 1-(2-Chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrile

HRID 1038845

Reaktionsgleichung

Reaktionsgleichung von HRID 1038845
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]#[N:19])[CH2:14][CH2:13]1>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]#[N:19])[CH2:14][CH2:13]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 1382234-CyanopiperidineHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidine

Produkt 1

HCID 866651101-(2-Chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrileAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 2,4-dichlorofuro[3,2-d]pyrimidine (0.40 g, 2.1 mmol, ArkPharm), piperidine-4-carbonitrile (0.23 g, 2.1 mmol, Oakwood) and TEA (0.59 mL, 4.2 mmol) in 1,4-dioxane (10 mL) was stirred at about 25° C. for about 12 h. The solvent was removed under reduced pressure and water (5 mL) and DCM (10 mL) were added to the residue. The layers were separated and the organic solution was concentrated under reduced pressure to give 1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrile (0.50 g, 90%): LC/MS (Table 2, Method 1) Rt=0.76 min; MS m/z: 263 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure and water (5 mL) and DCM (10 mL)
  2. additionwere added to the residue
  3. customThe layers were separated
  4. concentrationthe organic solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f1b6dfa90d5b464cab405f3abfa1d06a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551981B2

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