Sodium Hydroxide → tert-Butyl 2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1193353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193353
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].CN([CH:14]=[C:15]1[C:20](=O)[CH2:19][CH2:18][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16]1)C.[OH-].[Na+]>O>[CH3:6][S:7][C:8]1[N:9]=[CH:14][C:15]2[CH2:16][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:19][C:20]=2[N:10]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Produkt 1

HCID 22710609tert-Butyl 2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

S-Methylisothiourea sulfate (16.44 g, 59.06 mmol, 1.5 eq.) and tert-butyl 3-((dimethylamino)-methylene)-4-oxopiperidine-1-carboxylate (10.0 g, 39.37 mmol, 1.0 eq.) were taken up in water (40 ml); 1 M NaOH solution (50 ml) was added and stirring was carried out for 1 hour at 80° C. After monitoring by TLC, the reaction mixture was diluted with water (100 ml) and extracted with DCM (2×150 ml). The combined org. phases were washed with sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 25% ethyl acetate in hexane). Yield: 40% (4.5 g, 16.01 mmol)

Aufarbeitung

  1. extractionextracted with DCM (2×150 ml)
  2. washphases were washed with sat. NaCl solution (100 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, 25% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e862b422b0474663ba1dd5449de8d4db
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

Notizen zur Reaktion

Wird geladen…