Hydrochloric Acid → Ethyl 4-chloro-6-((4-methoxybenzyl)amino)pyrimidine-5-carboxylate

HRID 1052387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052387
N/[CH:2]=[N:3]/[C:4](/[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[C:5](\[C:11]#[N:12])/[C:6]([O:8][CH2:9][CH3:10])=[O:7].[ClH:23]>O>[Cl:23][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:3]=[CH:2][N:12]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 140693035ethyl (E)-3-[(E)-aminomethylideneamino]-2-cyano-3-[(4-methoxyphenyl)methylamino]prop-2-enoate

Produkt 1

HCID 90102730Ethyl 4-chloro-6-((4-methoxybenzyl)amino)pyrimidine-5-carboxylateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(E)-Ethyl 3-((E)-(aminomethylene)amino)-2-cyano-3-((4-methoxybenzyl)amino)acrylate (1.24 g, 3.49 mmol) was dissolved in 23 mL hydrochloride acid (4M in dioxane, 90.64 mmol) and the mixture was stirred at room temperature overnight. The mixture was poured into 400 mL water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified using SP1® Purification System (0% to 25%, hexane-ethyl acetate) to give 376 mg (34% yield) of the title compound as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude was purified
  7. customSP1® Purification System (0% to 25%, hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-dab59a736b124f109e6db94f7879fa36
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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