Hydrochloric Acid → 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methyl-1H-pyrazol-3-yl)-5-(thiophen-3-yl)-3,4-dihydropyrimidin-2(1H)-one

HRID 924876

Reaktionsgleichung

Reaktionsgleichung von HRID 924876
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=[N:3]1.[OH:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[O:27][CH3:28].[NH2:29][C:30]([NH2:32])=[O:31].Cl.[CH3:34]CO>>[CH2:28]([O:27][C:17]1[CH:18]=[C:19]([CH:20]2[C:8]([C:9]3[CH:13]=[CH:12][S:11][CH:10]=3)=[C:7]([C:4]3[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:22]=[C:23]([N+:24]([O-:26])=[O:25])[C:16]=1[OH:15])[CH3:34]

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1176UreaHCID 811345-NitrovanillinHCID 651950761-(1-methyl-1H-pyrazol-3-yl)-2-(thiophen-3-yl)ethanone2×

Produkt 1

HCID 513490824-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methyl-1H-pyrazol-3-yl)-5-(thiophen-3-yl)-3,4-dihydropyrimidin-2(1H)-oneAusbeute 81 %

Versuchsvorschrift

A mixture of 1-(1-methyl-1H-pyrazol-3-yl)-2-(thiophen-3-yl)ethanone (Intermediate 58) (750 mg, 3.6 mmol), 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (782 mg, 3.7 mmol), urea (666 mg, 11.1 mmol) and conc. HCl (0.2 mL) in EtOH (10 mL) was refluxed overnight. The mixture was concentrated under reduced pressure to dryness and purified by prep-HPLC (0.1% TFA as additive) to give Compound 119 (1.3 g, yield 81%). 1H NMR and MS (ESI) characterization included for the individual enantiomers, see Compound 149 and Compound 150.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. concentrationThe mixture was concentrated under reduced pressure to dryness
  3. custompurified by prep-HPLC (0.1% TFA as additive)

Quellen und Nachweise

ORD-Eintrag
ord-3ebb99111b514f4799c2c1261a3336c5
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283229B2

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