4-[4,6-Dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholine → 2-Phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amide

HRID 8607

Reaktionsgleichung

Reaktionsgleichung von HRID 8607
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[C:6]([Cl:17])[N:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1.[K].[C:25]1([CH2:31][CH2:32][S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CS(C)=O.O>[Cl:17][C:6]1[N:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=[C:2]([NH:36][S:33]([CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:34])=[O:35])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1

Komponenten

5

Edukt 2

HCID 219837204-[4,6-Dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholineHCID 688981502-Phenyl-ethanesulfonic acid amide potassium salt

Produkt 1

HCID 865924722-Phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amideAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-[4,6-dichloro-5-(3-methoxy-phenoxy)-pyrimidin-2-yl]-morpholine (1.0 g) and 2-phenyl-ethanesulfonic acid amide potassium salt (1.57 g, Referential Example 1e) in DMSO (15 ml) was stirred at 60° C. for 24 h. The solution was diluted with water (75 ml) and extracted twice with diethyl ether (75 ml) before it was acidified with 10% aq. citric acid. The mixture was extracted twice with EA (150 ml). The organic phase was washed with water (50 ml). The product precipitated upon evaporation of the solvent. The solid was collected, washed with diethyl ether and dried to give 2-phenyl-ethanesulfonic acid [6-chloro-5-(3-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amide (1.28 g) as off-white powder. LC-MS: tR=5.34 min, [M+1]+=505.12, [M−1]−=502.97.

Aufarbeitung

  1. extractionextracted twice with diethyl ether (75 ml) before it
  2. extractionThe mixture was extracted twice with EA (150 ml)
  3. washThe organic phase was washed with water (50 ml)
  4. customThe product precipitated upon evaporation of the solvent
  5. customThe solid was collected
  6. washwashed with diethyl ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-50b2dcef9ed84e548750be65d0cf0b62
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091201B2

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