Acetone, oxime → 3-(2,4-Diaminopteridin-6-yl)phenol

HRID 639169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639169
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([CH:10]=O)=O)[CH:5]=[CH:6][CH:7]=1.CC(=NO)C.S(O)(O)(=O)=O.[NH2:22][C:23]1[N:28]=[C:27]([NH2:29])[C:26]([NH2:30])=[C:25]([NH2:31])[N:24]=1.C(=O)(O)[O-].[Na+]>O.Cl>[NH2:22][C:23]1[N:28]=[C:27]([NH2:29])[C:26]2[C:25](=[N:31][CH:10]=[C:8]([C:4]3[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=3)[N:30]=2)[N:24]=1

Komponenten

7

Edukt 4

HCID 67180Acetone, oximeHCID 793582,4,5,6-Pyrimidinetetramine sulfate (1:1)HCID 516892Sodium BicarbonateHCID 129108752-(3-Hydroxyphenyl)-2-oxoacetaldehyde

Produkt 1

HCID 177510633-(2,4-Diaminopteridin-6-yl)phenolAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-Hydroxyphenylglyoxal (2.10 g, 12.5 mmol) was dissolved in 100 mL of DI water. Acetone oxime (0.912 g, 12.5 mmol) was added, followed by 3 drops of 1N aqueous hydrochloric acid to bring the pH to ca. 2-3. This solution was stirred at 50° C. for one hour, then 2,4,5,6-tetraminopyrimidine sulfate (2.67 g, 11.2 mmol) was added and the reaction mixture was stirred at ambient temperature for 3 hours, then brought to reflux and refluxed for 6 hours. At this point it formed a thick yellow suspension. The reaction was allowed to cool down to ambient temperature. Saturated aqueous sodium bicarbonate was added dropwise to bring the pH to ca. 6-7. The precipitate was collected, washed extensively with water, then with 60 mL of methanol and repeatedly with diethyl ether and dried in vacuo to give 2.75 g of the title compound (96.5% yield) as a light-yellow solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at ambient temperature for 3 hours
  2. temperatureto reflux
  3. temperaturerefluxed for 6 hours
  4. customAt this point it formed a thick yellow suspension
  5. temperatureto cool down to ambient temperature
  6. customThe precipitate was collected
  7. washwashed extensively with water
  8. dry with materialwith 60 mL of methanol and repeatedly with diethyl ether and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-443b107d6b7545b496d6540ff8753026
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691858B2

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