StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium ethoxide → Tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate

HRID 1921982
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1921982
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=2)=O.Cl.[CH3:34][N:35](N)[C:36]([NH2:38])=[NH:37].[O-]CC.[Na+]>C(O)C>[CH3:18][O:17][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[C:7]([C:5]3[CH:4]=[CH:3][N:38]=[C:36]([NH:35][CH3:34])[N:37]=3)[CH:8]=[C:9]2[N:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:23][CH2:24]2)=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxide2×HCID 21432264Methyl amino guanidine hydrochlorideHCID 67306919(E)-tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate

Produkt 1

HCID 53257824Tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel
2×

Versuchsvorschrift

To a solution of tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate 108 (1.5 g) in ethanol (50 ml) was added methyl amino guanidine hydrochloride (0.75 g) and 21% wt sodium ethoxide in ethanol (1 ml). The reaction was stirred at reflux for 2 days, and more sodium ethoxide (0.5 ml) was added to the reaction. The reaction was allowed to reflux overnight. The solvents were concentrated under reduced pressure and the residue was redissolved in ethyl acetate (100 ml) and water (50 ml). The organics were separated, washed with water (1×50 ml), dried over sodium sulfate and concentrated. Column chromatography (pre-packed SiO2, 40% ethyl acetate in hexanes to 75% ethyl acetate in hexanes) gave tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate 111 as a light yellow solid. LC/MS (m/z): 450 [M+H].

Aufarbeitung

  1. temperatureat reflux for 2 days
  2. temperatureto reflux overnight
  3. concentrationThe solvents were concentrated under reduced pressure
  4. dissolutionthe residue was redissolved in ethyl acetate (100 ml)
  5. customThe organics were separated
  6. washwashed with water (1×50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1e401605b6584671998960ac8640d5e1
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08173808B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion