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

Hydrochloric Acid → 4'-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone

HRID 1579316
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1579316
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([C:19](=[O:25])[CH2:20]S(C)(=O)=O)=[C:12]([O:26][CH2:27][CH3:28])[CH:11]=2)=[CH:4][N:3]=1.[Al].Cl>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:26][CH2:27][CH3:28])[C:13]([C:19](=[O:25])[CH3:20])=[C:14]([O:16][CH2:17][CH3:18])[CH:15]=2)=[CH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 5359268Aluminum2×HCID 232770301-[4-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,6-diethoxyphenyl]-2-methylsulfonylethanone

Produkt 1

HCID 232763584'-[(2,4-Diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 5.8 g. of 4'-[(2,4-diamino-5-pyrimidinyl)-methyl] -2',6'-diethoxy-2-(methylsulfonyl)acetophenone in 50 ml. of 20% aqueous tetrahydrofuran is reduced with 1 g. of amalgamated aluminum at 65° over a period of 4 hours. (The aluminum chips are immersed in a 2% hydrochloric acid solution for 2 minutes, rinsed with methanol, and thereafter used in the reduction.) The reaction mixture is filtered warm, the filtrate is concentrated and adjusted to a pH of 9 with 5% sodium hydroxide. The resulting solution is then shaken with five 50 ml. portions of ethyl acetate. The resulting crude product after column chromatography (200 g. of silica gel, elution solvent comprising chloroform/N-propanol/concentrated ammonium hydroxide, 80:20:1) yields 4'-[(2,4-diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-acetophenone, having a m.p. of 229°-231° recrystallized from methanol.

Aufarbeitung

  1. additionA suspension of 5.8 g
  2. washrinsed with methanol
  3. filtration) The reaction mixture is filtered
  4. temperaturewarm
  5. concentrationthe filtrate is concentrated
  6. washThe resulting crude product after column chromatography (200 g. of silica gel, elution solvent comprising chloroform/N-propanol/concentrated ammonium hydroxide, 80:20:1)

Quellen und Nachweise

ORD-Eintrag
ord-732863ce30e940678da669ce641395cf
Quelldatensatz
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03931181

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion