2-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine → 2-(4-Carboxy-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

HRID 388360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388360
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])=[CH:15][C:14]=2[O:29][CH3:30])[N:3]=1>C1COCC1.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[O:29][CH3:30])[N:3]=1

Komponenten

4

Edukt 1

HCID 582010032-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

Produkt 1

HCID 589063992-(4-Carboxy-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzyl 4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-benzoate (A3-a) (1.3 g, 3 mmol) is suspended in a hydrogenating autoclave in 50 mL THF and mixed with Pd(OH)2 on charcoal (180 mg, charge 20%, approx. 50% water). Then 4.5 bar H2 pressure are applied and the reaction mixture is stirred for 24 h. After the reaction has ended the reaction mixture is filtered, the filtrate is evaporated down and the crude product A-4a (HPLC-MS: tRet.=1.24 min; MS (M−H)+=346) is used in the subsequent reactions without any further purification.

Aufarbeitung

  1. filtrationis filtered
  2. customthe filtrate is evaporated down
  3. customthe crude product A-4a (HPLC-MS: tRet.=1.24 min; MS (M−H)+=346) is used in the subsequent reactions without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-d36a0358c14646519c09fb502ebc7aba
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377943B2

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