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Methanol → 2-[Bis(tert-butoxycarbonyl)amino)-5-(2'-methylsulfonylphenyl)pyrimidine

HRID 610127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 610127
[C:1]([O:5][C:6]([N:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2SC)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:31][S:32]([O-:34])=O.[K+].[CH3:36]O>O>[C:1]([O:5][C:6]([N:8]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:32]([CH3:36])(=[O:34])=[O:31])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 181773202-[Bis(tert-butoxycarbonyl)amino]-5-(2'-methylthiophenyl)pyrimidineHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 181772932-[Bis(tert-butoxycarbonyl)amino)-5-(2'-methylsulfonylphenyl)pyrimidineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-[Bis(tert-butoxycarbonyl)amino]-5-(2'-methylthiophenyl)pyrimidine (2.13 g, 5.1 mmol) was dissolved in MeOH (20 mL) and cooled to 0° C. In a separate beaker, a solution of Oxone (5.49 g) was generated by dilution to 27 mL with water. A portion of this solution (17 mL, 5.6 mmol) was removed and adjusted to pH 4.2 with sat. Na3PO4 solution (4.7 mL). This mixture was added to the reaction and stirred 23 hours at room temp. The resulting mixture was diluted with water and extracted with CHCl3. The organics were combined, washed with water and brine, dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel (50-100% EtOAc/hexanes) to yield the sulfone (1.28 g, 56%). 1H NMR (CDCl3): δ8.81 (s, 2H) , 8.28 (dd, 1H, J=7.6, J'=1.4), 7.72 (m, 2H), 7.39 (dd, 1H, J=7.3, J'=1.4), 2.76 (s, 3H), 1.50 (s, 18H).

Aufarbeitung

  1. additionThis mixture was added to the reaction
  2. extractionextracted with CHCl3
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on silica gel (50-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e171e78f58734aee905f2b912990593b
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05998424

Notizen zur Reaktion

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