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 2177970

반응식

HRID 2177970 반응식
[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]

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1176UreaHCID 811345-NitrovanillinHCID 651950761-(1-methyl-1H-pyrazol-3-yl)-2-(thiophen-3-yl)ethanone2회

생성물 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)-one수율 81%

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-70a00d89ffb4435981cc4581dfa8913a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067893B2

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