Succinyl chloride → 1-[4-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-pyrrolidine-2,5-dione

HRID 1161693

Reaktionsgleichung

Reaktionsgleichung von HRID 1161693
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[C:23](Cl)(=[O:29])[CH2:24][CH2:25][C:26](Cl)=[O:27]>CN(C)C=O.CN(C1C=CN=CC=1)C.O>[Cl:16][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[CH:5]=[C:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=[C:2]([N:1]3[C:26](=[O:27])[CH2:25][CH2:24][C:23]3=[O:29])[N:7]=2)[CH:14]=[CH:13][C:12]=1[OH:15]

Komponenten

6

Edukt 2

HCID 10970Succinyl chlorideHCID 586261414-(2-Amino-6-phenyl-pyrimidin-4-ylamino)-2-chloro-phenol

Produkt 1

HCID 115892931-[4-(3-Chloro-4-hydroxy-phenylamino)-6-phenyl-pyrimidin-2-yl]-pyrrolidine-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compound 4-(2-amino-6-phenyl-pyrimidin-4-ylamino)-2-chloro-phenol (0.5 g, 1.6 mmol) in dry dimethylformamide (10 mL) was added 4-(N,N-dimethylamino)pyridine (0.39 g, 3.2 mmol) at 0° C. with stirring under nitrogen atmosphere. To this was added freshly prepared succinyl chloride (0.62 g, 4 mmol). The mixture was then stirred at 80° C. for 20 hours. After completion of the reaction the mixture was diluted with water (75 mL), the solid separated was filtered off, washed with cold water (200 mL) and dried. The solid was purified further by column chromatography using petroleum ether-ethyl acetate to give the desired product as a light brown solid.

Aufarbeitung

  1. stirringThe mixture was then stirred at 80° C. for 20 hours
  2. customAfter completion of the reaction the mixture
  3. customthe solid separated
  4. filtrationwas filtered off
  5. washwashed with cold water (200 mL)
  6. customdried
  7. customThe solid was purified further by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-00aa9bc38e134df8ab973a9e9f70ce33
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820654B2

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