Benzylamine → 4-N-benzyl-6-chloropyrimidine-2,4-diamine

HRID 2367174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367174
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.CCN(C(C)C)C(C)C.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(C)=O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=1

Komponenten

6

Edukt 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 655222-Amino-4,6-dichloropyrimidineHCID 81531Diisopropylethylamine

Produkt 1

HCID 14842704-N-benzyl-6-chloropyrimidine-2,4-diamineAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 4,6-dichloro-2-pyrimidinamine (0.5 g, 3.1 mmol) in EtOH (10 mL) was added Hunig's base (1.1 mL, 6.1 mmol) followed by benzylamine (0.37 mL, 3.35 mmol) and the reaction mixture was stirred overnight at 100° C. The reaction mixture was poured onto water and EtOAc. The organic layer was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the crude title compound (670 mg) as a yellow solid. LC-MS (ES) m/z=235 [M+H]+.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b9457f9a7b1c46bc8bd9e3da06095b79
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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