Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine

HRID 1352775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352775
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].C(N(CC)CC)C.[C:19]([C:22]1[C:23]([Cl:30])=[N:24][C:25]([Cl:29])=[N:26][C:27]=1Cl)([OH:21])=[O:20]>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH:6][C:27]1[C:22]([C:19]([OH:21])=[O:20])=[C:23]([Cl:30])[N:24]=[C:25]([Cl:29])[N:26]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 200839572,4,6-Trichloropyrimidine-5-carboxylic acid

Produkt 1

HCID 178482874-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidineAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 311Citric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A N,N-dimethylformamide solution 6 ml of 3-chloro-4-methoxybenzylamine 1.51 g and triethylamine 2.46 g is dropped over a period of 25 minutes under ice cooling a solution of 5-carboxy-2,4,6-trichloropyrimidine (prepared in Example 318 (1)) 2.00 g in N,N-dimethylformamide 12 ml, and the mixture is further stirred for 90 minutes. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The combined extract is washed with water and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-2,6-dichloropyrimidine-5-carboxylic acid as a pale brown crystalline powder 2.92 g. mp 144–151° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe combined extract
  3. washis washed with water
  4. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f560935b3cda4c13a9000856a529ea7e
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220736B2

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