2-Chloro-N4-methylpyrimidine-4,5-diamine → 2-chloro-6-(3,5-dimethoxyphenyl)-8-methylpteridin-7(8H)-one

HRID 524046

Reaktionsgleichung

Reaktionsgleichung von HRID 524046
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[C:12]([O:14]CC)=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:18][C:19]1[N:24]=[C:23]([NH:25][CH3:26])[C:22]([NH2:27])=[CH:21][N:20]=1>C(O)C.C(O)(=O)C.ClCCl>[Cl:18][C:19]1[N:20]=[CH:21][C:22]2[N:27]=[C:11]([C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:12](=[O:14])[N:25]([CH3:26])[C:23]=2[N:24]=1

Komponenten

6

Edukt 2

HCID 71471722-Chloro-N4-methylpyrimidine-4,5-diamineHCID 24722256Ethyl (3,5-dimethoxyphenyl)(oxo)acetate

Produkt 1

HCID 867135722-chloro-6-(3,5-dimethoxyphenyl)-8-methylpteridin-7(8H)-oneAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 2-(3,5-dimethoxyphenyl)-2-oxoacetate (1 g, 4.2 mmol) and 2-chloro-N4-methylpyrimidine-4,5-diamine (600 mg, 3.8 mmol) in ethanol (100 mL) and acetic acid (2.5 mL) was stirred at 80° C. for 48 h and cooled to RT (5° C.). The mixture was diluted with dichloromethane and washed with brine. The organic layer was directly concentrated and purified by chromatography on silica gel to give the title compound (700 mg, 50%). MS (ES+) C15H13ClN4O3 requires: 332, 334. found: 333, 335 [M+H]+.

Aufarbeitung

  1. temperaturecooled to RT (5° C.)
  2. washwashed with brine
  3. concentrationThe organic layer was directly concentrated
  4. custompurified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c7cfbcd3f50444029c2e3d5ba79ae584
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340514B2

Verknüpfte Notizen

Wird geladen…