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 401087

反応式

HRID 401087 の反応式
[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]

参加物

6

反応物 5

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

生成物 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)-one収率 81%

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ddd4191c03bf4694b408aad1997bc684
出典データセット
uspto-grants-2014_06
特許番号
US08741915B2

関連ノート

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