Cesium carbonate → 2-(6-((1S,2S)-2-((6-chloro-2-methylpyrimidin-4-yloxy)methyl)cyclopropyl)pyridin-3-yl)propan-2-ol

HRID 2175416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175416
[OH:1][CH2:2][C@H:3]1[CH2:5][C@@H:4]1[C:6]1[N:11]=[CH:10][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([CH3:24])[N:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:16][C:17]1[N:18]=[C:19]([CH3:24])[N:20]=[C:21]([O:1][CH2:2][C@H:3]2[CH2:5][C@@H:4]2[C:6]2[N:11]=[CH:10][C:9]([C:12]([OH:15])([CH3:13])[CH3:14])=[CH:8][CH:7]=2)[CH:22]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 712743282-(6-((1S,2S)-2-(Hydroxymethyl)cyclopropyl)pyridin-3-yl)propan-2-ol

Produkt 1

HCID 867295742-(6-((1S,2S)-2-((6-chloro-2-methylpyrimidin-4-yloxy)methyl)cyclopropyl)pyridin-3-yl)propan-2-olAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of compound 8-2 (135 mg, 0.652 mmol) and 4,6-dichloro-2-methylpyrimidine (106.3 mg, 0.65 mmol) in THF (3.0 mL) was treated with Cs2CO3 (281 mg, 0.86 mmol) and heated to reflux for 12 h. The reaction mixture was filtrated and the filtrate was concentrated and purified directly by gradient elution on silica gel (Petroleum ether:ethyl acetate=2:1-1:1) to afford the title compound as a colorless oil (60 mg, 28%). LRMS (ES) calculated M+H for C17H20ClN3O2: 334.12. Found: 334.1.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. filtrationThe reaction mixture was filtrated
  4. concentrationthe filtrate was concentrated
  5. custompurified directly by gradient elution on silica gel (Petroleum ether:ethyl acetate=2:1-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-fc48a6758fe54b259a770e2ddbb9c16e
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062059B2

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