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Ammonium Chloride → t-Butyl [3-(4,6-dimethoxypyrimidin-2-ylmethyl)-2-pyridyl]carbamate

HRID 1418817
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1418817
C([Li])CCC.[CH3:6][C:7]1[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([CH2:6][C:7]2[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[N:9][CH:10]=[CH:11][CH:12]=2)[N:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 117458482-(N-Boc-Amino)-3-methylpyridineHCID 178418339Butyllithium

Produkt 1

HCID 53782638t-Butyl [3-(4,6-dimethoxypyrimidin-2-ylmethyl)-2-pyridyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

n-Butyllithium (19.2 ml of a 2.5M solution in hexane) was added dropwise to a stirred suspension of the product of stage (a) above (5.0 g) in dry tetrahydrofuran (100 ml) under nitrogen at -70° C. The mixture was stirred at -70° C. for 20 minutes and then at 5° C. for 3 hours. It was then cooled to -70° C. and treated with 4,6-dimethoxy-2-methylsulfonylpyrimidine (5.42 g), and the mixture was stirred at -70° C. for 1 hour, then at room temperature overnight. Saturated ammonium chloride solution (500 ml) was added, and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml), dried and evaporated to give an orange oil which was triturated with hexane to give 5.35 g of the desired product as a pale yellow solid, mp 89°-92° C.

Aufarbeitung

  1. waitat 5° C. for 3 hours
  2. temperatureIt was then cooled to -70° C.
  3. stirringthe mixture was stirred at -70° C. for 1 hour
  4. customat room temperature
  5. customovernight
  6. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  7. washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
  8. customdried
  9. customevaporated
  10. customto give an orange oil which
  11. customwas triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-3dfb63236e5942579a342a0ca48fa300
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05885935

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