Potassium Carbonate → ethyl 2-((1S,4S)-5-benzhydryl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyrimidine-5-carboxylate

HRID 1946596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946596
Cl.Cl.[CH:3]([N:16]1[CH2:21][C@@H:20]2[CH2:22][C@H:17]1[CH2:18][NH:19]2)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS([C:27]1[N:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:28]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[CH:3]([N:16]1[CH2:21][C@@H:20]2[CH2:22][C@H:17]1[CH2:18][N:19]2[C:27]1[N:28]=[CH:29][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][N:32]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylateHCID 67006897HCID 67006897, Verbindung

Produkt 1

HCID 67007769ethyl 2-((1S,4S)-5-benzhydryl-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyrimidine-5-carboxylateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Title compound 201 (0.250 g, 0.741 mmol), ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (0.122 g, 0.529 mmol), potassium carbonate (0.280 g, 2.645 mmol) and DME (5 mL) were combined. The reaction mixture was stirred at 50 oC for 2 hours. The mixture was cooled down and quench with water. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography eluting with 0% to 30% ethyl acetate in hexanes to afford title compound 202 (0.141 g, 64%). LRMS (ESI): (calc) 414.21 (found) 415.0 (MH)+.

Aufarbeitung

  1. temperatureThe mixture was cooled down
  2. customquench with water
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by flash chromatography
  9. washeluting with 0% to 30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3436d06ae4a941c396b3ed0b042857c7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399452B2

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