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Triethylamine → Ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate

HRID 1798899
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1798899
Cl[C:2]1[C:3]2[C:13](=[O:14])[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.C(N(CC)CC)C.O.[NH2:34][NH2:35]>O1CCOCC1>[NH:34]([C:2]1[C:3]2[C:13](=[O:14])[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1)[NH2:35]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 59506342Ethyl 4-chloro-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate

Produkt 1

HCID 59506527Ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylateAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of ethyl 4-chloro-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate (21 g, 55.57 mmol) in 1,4-dioxane (400 mL) was added triethylamine (8.52 mL, 61.13 mmol) followed by hydrazine hydrate (3.06 g, 61.13 mmol). The reaction mixture was stirred at room temperature for 5-6 h. Upon completion of the reaction, dioxane was removed under reduced pressure and water (250 mL) was added to the reaction mixture. The reaction mixture was then extracted with dichloromethane (200 mL×3). The combined organic layers was washed with water (500 mL) followed by brine (500 mL), dried over anhydrous Na2SO4, filtered and concentrated to give crude ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate (20 g) which was used in the next step without purification. LCMS [M+H]: 374

Aufarbeitung

  1. customwas removed under reduced pressure and water (250 mL)
  2. additionwas added to the reaction mixture
  3. extractionThe reaction mixture was then extracted with dichloromethane (200 mL×3)
  4. washThe combined organic layers was washed with water (500 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9dade497f401400891085d5ca438a049
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343983B2

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