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Sulfuric Acid → Methyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetate

HRID 2387812
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2387812
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#N)=[CH:12][C:11]=2[O:19][CH3:20])=[C:4]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:3]=1.S(=O)(=O)(O)[OH:28].[C:32]([O-])(O)=[O:33].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:33][CH3:32])=[O:28])=[CH:12][C:11]=2[O:19][CH3:20])=[C:4]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 689540842-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Produkt 1

HCID 42613073Methyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The product from step (vii) (0.329 g) was added in one portion to a mixture of sulfuric acid (2 ml) and MeOH (4 mL). The resulting solution was stirred at 70° C. for 2 h. The mixture was allowed to cool and poured into saturated aqueous NaHCO3 (20 mL). The aqueous was extracted with EtOAc and the combined organic phase was dried, filtered and evaporated. The crude product was purified by RPHPLC to afford a colourless gum that was triturated with hexane (5 mL). The solid was collected by filtration to give the title compound as a colorless solid 0.089 g.

Aufarbeitung

  1. temperatureto cool
  2. extractionThe aqueous was extracted with EtOAc
  3. customthe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by RPHPLC
  7. customto afford a colourless gum that
  8. customwas triturated with hexane (5 mL)
  9. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1f3617a988a1454d81ce7d49addb3559
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08268990B2

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