Potassium Carbonate → 4-Chloro-2-cyclopropyl-6-(3-fluoro-azetidin-1-yl)-pyrimidine

HRID 1984310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984310
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH:9]2[CH2:11][CH2:10]2)[N:3]=1.Cl.[F:13][CH:14]1[CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>COCC(O)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:16]2[CH2:17][CH:14]([F:13])[CH2:15]2)[N:3]=[C:4]([CH:9]2[CH2:11][CH2:10]2)[N:5]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 101250543-fluoroazetidine HydrochlorideHCID 249036874,6-Dichloro-2-cyclopropylpyrimidine

Produkt 1

HCID 101491454-Chloro-2-cyclopropyl-6-(3-fluoro-azetidin-1-yl)-pyrimidineAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 79001-Methoxy-2-propanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 4,6-dichloro-2-cyclopropylpyrimidine 19 (1.05 g, 5.5 mmol), 3-fluoroazetidine hydrochloride 162 (0.68 g, 6 mmol) and potassium carbonate (2.48 g, 18 mmol) in 1-methoxy-2-propanol (10 ml) is heated at 65° C. for 2 hours. The mitre is cooled, concentrated in vacuo, diluted with dichloromethane and washed three times with water. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo to afford 4-chloro-2-cyclopropyl-6-(3-fluoro-azetidin-1-yl)-pyrimidine 163 (1.16 g, 92%) as a yellow oil which is used in the next step without further purification.

Aufarbeitung

  1. temperatureThe mitre is cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with dichloromethane
  4. washwashed three times with water
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d748d46600664003a6b506f0638c3878
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544675B2

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