Triethylamine → [1-(4-Methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine

HRID 339795

Reaktionsgleichung

Reaktionsgleichung von HRID 339795
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].O1CCO[CH:13](O)[CH:12]1O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1.C(N(CC)CC)C>CCO.CCCCCC.CCOC(C)=O>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([NH:29][C:2]2[C:3]3[C:4](=[N:9][CH:12]=[CH:13][N:10]=3)[N:5]=[C:6]([CH3:8])[N:7]=2)[CH3:28])=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 961701,4-Dioxane-2,3-diolHCID 2381811-(4-Methoxyphenyl)ethanamineHCID 5941456-Chloro-2-methylpyrimidine-4,5-diamine

Produkt 1

HCID 58174228[1-(4-Methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amineAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 6-chloro-4,5-diamino-2-methylpyrimidine (317 mg, 2.0 mmol) and 1,4-dioxane-2,3-diol (240 mg, 2.0 mmol) in EtOH (15 mL) was stirred at 25° C. for 1 h. TLC analysis (1:1 hexane/EtOAc on SiO2) indicated complete consumption of starting material. 1-(4-Methoxyphenyl)-ethylamine (332 mg, 2.2 mmol) and triethylamine (Et3N, 0.3 mL, 2.2 mmol) were added, and the reaction was stirred overnight. The majority of solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was concentrated in vacuo to leave a brown residue that was purified by column chromatography over SiO2, eluting with 2:1 EtOAc/hexane, then 100% EtOAc to afford [1-(4-methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine (126 mg) as a brown oil.

Aufarbeitung

  1. customconsumption of starting material
  2. stirringthe reaction was stirred overnight
  3. customThe majority of solvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc and H2O
  5. concentrationThe organic layer was concentrated in vacuo
  6. customto leave a brown residue that
  7. customwas purified by column chromatography over SiO2
  8. washeluting with 2:1 EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f24ae463ec024ff493a47364f93602d2
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895568B2

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