Guanidine Hydrochloride → 4-(2-Chloropyridin-3-yl)pyrimidin-2-amine

HRID 2361014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361014
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].[Cl:7][C:8]1[C:13]([C:14](=O)/[CH:15]=[CH:16]/N(C)C)=[CH:12][CH:11]=[CH:10][N:9]=1>CO>[Cl:7][C:8]1[C:13]([C:14]2[CH:15]=[CH:16][N:3]=[C:4]([NH2:6])[N:5]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Komponenten

5

Edukt 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 161089731-(2-Chloropyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one

Produkt 1

HCID 533963354-(2-Chloropyridin-3-yl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In an argon purged 500 mL round bottom flask placed in an isopropanol bath, was added sodium metal (3.40 g, 148 mmol) slowly to methanol (180 mL). The mixture was stirred at RT for about 30 minutes. To this was added guanidine hydrochloride (12.0 mL, 182 mmol) and the mixture was stirred at RT for 30 minutes, followed by addition of (E)-1-(2-chloropyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one (12.0 g, 57.0 mmol), attached air condenser, moved reaction to an oil bath, where it was heated to about 50° C. for 24 h. Approximately half of the methanol was evaporated under reduced pressure and the solids were filtered under vacuum, then washed with saturated NaHCO3 and H2O, air dried to yield 4-(2-chloropyridin-3-yl)pyrimidin-2-amine as off white solid. MS m/z=207 [M+1]+. Calc'd for C9H7ClN4: 206.63.

Aufarbeitung

  1. customIn an argon purged 500 mL round bottom flask
  2. customplaced in an isopropanol bath
  3. stirringthe mixture was stirred at RT for 30 minutes
  4. customreaction to an oil bath
  5. temperaturewhere it was heated to about 50° C. for 24 h
  6. customApproximately half of the methanol was evaporated under reduced pressure
  7. filtrationthe solids were filtered under vacuum
  8. washwashed with saturated NaHCO3 and H2O, air
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4a69eb7dfad04357845e4b16894be421
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08686155B2

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