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

HRID 2404029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404029
[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-15ecb518e3ba44c280e7db32c35f7a6a
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802697B2

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