3-Chlorobenzoic Acid → HCID 178478055, Verbindung

HRID 1397616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397616
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=O.P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:9]=[C:14]([C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([Cl:10])[CH:12]=1)[NH:8]2

Komponenten

4

Edukt 3

HCID 4473-Chlorobenzoic AcidHCID 24813Phosphorus oxychlorideHCID 780104,5-Pyrimidinediamine, 6-chloro-

Produkt 1

HCID 178478055HCID 178478055, VerbindungAusbeute 99,8 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 6-Chloro-4,5-diaminopyrimidine (0.70 g, 4.84 mmol) and 3-chlorobenzoic acid (0.76 g, 4.84 mmol) in the flask was added phosphoryl chloride (40.0 mL), and the resulting mixture was stirred for 16 h at 100° C. The reaction mixture was evaporated to remove excess phosphoryl chloride, and the residue was added to water (20 mL). The precipitate was filtered and purified by flash chromatography (0 to 5% Methanol/DCM) to afford the title compound (1.28 g, 31%) as a yellow solid. LC/MS: Rt=1.59 min, ES+ 265.0 (FA standard).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customto remove excess phosphoryl chloride
  3. additionthe residue was added to water (20 mL)
  4. filtrationThe precipitate was filtered
  5. custompurified by flash chromatography (0 to 5% Methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-40b628a5272549259fa0b1d2da6a5958
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901136B2

Notizen zur Reaktion

Wird geladen…