Azetidine → Ethyl 6-(azetidin-1-ylmethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

HRID 1426312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426312
[NH:1]1[CH2:4][CH2:3][CH2:2]1.Br[CH2:6][C:7]1[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=1>C(Cl)Cl>[N:1]1([CH2:6][C:7]2[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 10422AzetidineHCID 58431340Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

Produkt 1

HCID 58431385Ethyl 6-(azetidin-1-ylmethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Azetidine (0.62 mL, 9.2 mmol, Aldrich) was added to a solution of ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (1.76 g, 4.16 mmol, prepared in the manner outlined in Example 47, Step A) in methylene chloride (39 mL). and the reaction was stirred for 20 minutes. Solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel, eluting with a gradient from 0-5% MeOH in DCM to afford product (0.74 g, 61%); LCMS (M+H)+: 290.0.

Aufarbeitung

  1. customprepared in the manner
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel
  4. washeluting with a gradient from 0-5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-f787872e370444099d1e4ca11b2bae0a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933085B2

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