4,5-Pyrimidinediamine, 6-chloro- → 6-Chloro-8-(2,6-dichloro-benzyl)-9H-purine

HRID 474303

Reaktionsgleichung

Reaktionsgleichung von HRID 474303
[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:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[CH2:18][CH:19]=O>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:9]=[C:19]([CH2:18][C:12]1[C:11]([Cl:10])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:17])[NH:8]2

Komponenten

4

Edukt 2

HCID 780104,5-Pyrimidinediamine, 6-chloro-HCID 122635642-(2,6-Dichlorophenyl)acetaldehyde

Produkt 1

HCID 1784780976-Chloro-8-(2,6-dichloro-benzyl)-9H-purineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 6-chloro-pyrimidine-4,5-diamine (100 mg, 0.694 mmol), (2,6-dichloro-phenyl)-acetaldehyde (260 mg, 1.38 mmol) and 1,4-dioxane (7 mL) was added 5% FeCl3.SiO2 (150 mg). The resulting mixture was heated to 100° C. in a sealed tube. After 24 h, the mixture was cooled to rt and filtered through a pad of diatomaceous earth, washing with EtOAc (3×10 mL). The filtrate was concentrated and the residue was purified by preparative reverse-phase HPLC to afford the title compound as a white solid (25 mg, 36%). MS (ESI): mass calcd. for C12H7Cl3N4, 311.9; m/z found, 313.0 [M+H]+. 1H NMR (CDCl3): 8.65 (s, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.34-7.29 (m, 1H), 4.78 (s, 2H).

Aufarbeitung

  1. temperaturethe mixture was cooled to rt
  2. filtrationfiltered through a pad of diatomaceous earth
  3. washwashing with EtOAc (3×10 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b03d2813e45c4bb5a7f6ac074cc36c09
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637527B2

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