Cesium carbonate → 4-(4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide

HRID 522907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522907
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([NH:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[O:12][CH:10]1[CH2:11][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([NH:28][CH3:29])=[O:27])=[CH:30][CH:31]=3)[N:7]=2)[CH2:9]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 2355164-Amino-N-methylbenzamideHCID 866852552-Chloro-4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidine

Produkt 1

HCID 673551644-(4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidine (0.200 g, 609 mmoL) and 4-amino-N-methylbenzamide (0.109 g, 0.731 mmoL) in dimethyl acetamide (5 mL) was added cesium carbonate (300 mg, 9.14 mmol) and the reaction mixture was degassed for 15 min. Tris(dibenzylideneacetone)dipalladium (0) [Pd2(dba)3](0.030 g, 0.03 mmoL) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [BINAP] (0.020 g, 0.03 mmoL) were added and the mixture was irradiated in the microwave at 120° C. for 1 h. Then the reaction was quenched with water and extracted with EtOAc (2×25 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 4-(4-(3-(2,4-dichlorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide (0.077 g, 29%) as solid. Observed mass (M+1): 443.9.

Aufarbeitung

  1. customthe reaction mixture was degassed for 15 min
  2. additionTris(dibenzylideneacetone)dipalladium (0) [Pd2(dba)3](0.030 g, 0.03 mmoL) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [BINAP] (0.020 g, 0.03 mmoL) were added
  3. customthe mixture was irradiated in the microwave at 120° C. for 1 h
  4. customThen the reaction was quenched with water
  5. extractionextracted with EtOAc (2×25 mL)
  6. washThe organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eede4a1393374044915130319e99f6f7
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334269B2

Notizen zur Reaktion

Wird geladen…