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

HRID 401042노트

반응식

HRID 401042 반응식
[C:1]1([CH2:7][C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[NH2:31][C:32]([NH2:34])=[O:33].Cl>CCO>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH3:17]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 43289002-Phenyl-1-pyridin-3-yl-ethanone2회

생성물 1

HCID 569613494-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(pyridin-3-yl)-3,4-dihydropyrimidin-2(1H)-one수율 21%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-phenyl-1-(pyridin-3-yl)ethanone (Intermediate 31) (110 mg, 0.56 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (107 mg, 0.51 mmol), urea (91 mg, 1.52 mmol), and concentrated HCl solution (0.04 mL, 0.56 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was evaporated in vacuo and purified by preparative HPLC to give Compound 65 (46.21 mg, yield 21%). 1H NMR (DMSO-d6 400 MHz): δ 10.28 (s, 1H), 8.91 (s, 1H), 8.46 (d, J=5.2 Hz, 1H), 8.36 (s, 1H), 7.71 (d, J=7.2 Hz, 1H), 7.59 (s, 1H), 7.43 (s, 1H), 7.36 (t, J=5.2 Hz, 1H), 7.15 (s, 1H), 7.09-7.04 (m, 3H), 6.86 (d, J=6.8 Hz, 2H), 5.29 (d, J=2.0 Hz, 1H), 4.04 (q, J=6.8 Hz, 2H), 1.33 (t, J=6.8 Hz, 3H); MS (ESI): m/z 433.0 [M+1]+.

후처리

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated in vacuo
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-e49c6440131e4438b020ba0f4f9ac925
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741915B2

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