4-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde → HCID 89814189, Verbindung

HRID 522733

Reaktionsgleichung

Reaktionsgleichung von HRID 522733
[NH2:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([Br:12])=[C:6]([CH2:8][C:9](=O)[CH3:10])[CH:7]=1.[NH2:14][C:15]1[C:20]([CH:21]=O)=[CH:19][N:18]=[C:17]([S:23][CH3:24])[N:16]=1.[O-]CC.[Na+]>CCO>[Br:12][C:5]1[C:6]([C:8]2[C:9]([CH3:10])=[N:14][C:15]3[N:16]=[C:17]([S:23][CH3:24])[N:18]=[CH:19][C:20]=3[CH:21]=2)=[CH:7][C:2]([NH2:1])=[C:3]([F:13])[CH:4]=1

Komponenten

5

Edukt 3

HCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 2723922Sodium ethoxideHCID 898138911-(5-Amino-2-bromo-4-fluorophenyl)propan-2-one

Produkt 1

HCID 89814189HCID 89814189, VerbindungAusbeute 16,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Treat a solution of 1-(5-amino-2-bromo-4-fluorophenyl)propan-2-one (5 g, 27.62 mmol) and 4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (4.67 g, 27.62 mmol) in EtOH (30 mL) with sodium ethoxide (3.76 g, 55.25 mmol) and stir at RT for 12 h. Concentrate the mixture to dryness, treat with water, extract with EtOAc (3×), wash the combined organics with brine, dry with Na2SO4, concentrate and purify by silica gel chromatography (EtOAc/Pet Ether, 1:4) to afford the title compound (1.7 g, 16% yield). MS (m/z): 379.1/381.1 (M+1).

Aufarbeitung

  1. concentrationConcentrate the mixture to dryness
  2. additiontreat with water
  3. extractionextract with EtOAc (3×)
  4. washwash the combined organics with brine
  5. dry with materialdry with Na2SO4
  6. concentrationconcentrate
  7. custompurify by silica gel chromatography (EtOAc/Pet Ether, 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-a4a069c1044e4d92b8eea34500bf7c52
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334267B2

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