Potassium Carbonate → tert-Butyl 4-(((6-chloropyrimidin-4-yl)amino)methyl)piperidine-1-carboxylate

HRID 556802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556802
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][NH2:23])[CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:23][CH2:22][CH:19]2[CH2:20][CH2:21][N:16]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:17][CH2:18]2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 7368171-Boc-4-(aminomethyl)piperidine

Produkt 1

HCID 45787122tert-Butyl 4-(((6-chloropyrimidin-4-yl)amino)methyl)piperidine-1-carboxylateAusbeute 105,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4,6-Dichloropyrimidine (284 mg, 1.9 mmol), N-Boc-4-aminomethyl piperidine (409 mg, 1.9 mmol) and potassium carbonate (317 mg, 2.3 mmol) were dissolved in acetonitrile (5 mL) and the solution was heated for 30 minutes at 120° C. using microwave irradiation. The reaction mixture was partitioned between water and dichloromethane and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and evaporated to give tert-butyl 4-((6-chloropyrimidin-4-ylamino)methyl)-piperidine-1-carboxylate (656 mg, 100%) as a yellow oil which was used without further purification.

Aufarbeitung

  1. custommicrowave irradiation
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-72eb993ef4914bd9a3c1a4258aae1c1d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058045B2

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