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

HRID 446299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446299
[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 (used as a heat sink), added sodium metal (3.40 g, 148 mmol) slowly to methanol (180 mL). Stirred at RT for 30 minutes. Added guanidine hydrochloride (17.0 g, 182 mmol), stirred at RT for 30 minutes, added (E)-1-(2-chloropyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one (12.0 g, 57.0 mmol), attached air condenser, and heated to 50° C. for 24 hours. Removed approximately half of the methanol by rotary evaporation. Filtered solids onto side-armed flask 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+H)+=206. Calc'd′206.63 for C9H7ClN4.

Aufarbeitung

  1. customIn an argon purged 500 mL round bottom flask
  2. customplaced in an isopropanol bath
  3. temperatureheated to 50° C. for 24 hours
  4. customRemoved approximately half of the methanol
  5. customby rotary evaporation
  6. filtrationFiltered solids onto side-armed flask under vacuum
  7. washwashed with saturated NaHCO3 and H2O, air
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-466c7bf5b8454c0dbf830906fe899eba
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476434B2

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