Water → 2-[4-(2-Naphthalenylsulfonyl)-1-piperazinyl]-5-pyrimidinecarboxylic acid, ethyl ester

HRID 538085

Reaktionsgleichung

Reaktionsgleichung von HRID 538085
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].CS([C:26]1[N:31]=[CH:30][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][N:27]=1)(=O)=O.O>C1COCC1>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:26]2[N:27]=[CH:28][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][N:31]=2)[CH2:18][CH2:17]1)(=[O:15])=[O:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylateHCID 7039571-(Naphthalene-2-sulfonyl)-piperazine

Produkt 1

HCID 588449772-[4-(2-Naphthalenylsulfonyl)-1-piperazinyl]-5-pyrimidinecarboxylic acid, ethyl esterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

NaH 60% (0.0217 mol) was added portionwise at room temperature to a solution of 1-(2-naphtalenesulfonyl)-piperazine (0.011 mol) in THF (50 ml) under N2 flow. The mixture was stirred at room temperature for 1 hour, then cooled to 0° C. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.014 mol) in THF (30 ml) was added quickly. The mixture was stirred at room temperature for 2 hours, poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was taken up in diethyl ether. The precipitate was filtered off and dried, yielding 3.92 g (84%) of 2-[4-(2-naphthalenylsulfonyl)-1-piperazinyl]-5-pyrimidinecarboxylic acid, ethyl ester (interm. 8), melting point>260° C.

Aufarbeitung

  1. temperaturecooled to 0° C
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. filtrationThe precipitate was filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-04ddf9950e6b470aa8729598a55cb8aa
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865720B2

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