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

HRID 924840노트

반응식

HRID 924840 반응식
[C:1]1([CH2:7][C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[NH2:30][C:31]([NH2:33])=[O:32].Cl>CCO.O>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:21]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[NH:33][C:31](=[O:32])[NH:30]2)[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH3:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 6870902-Phenyl-1-(2-thienyl)ethanone2회

생성물 1

HCID 668261004-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(thiophen-2-yl)-3,4-dihydropyrimidin-2(1H)-one수율 23%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of 2-phenyl-1-(thiophen-2-yl)ethanone (Intermediate 38) (100 mg, 0.49 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (95 mg, 0.45 mmol), urea (81 mg, 1.35 mmol), and concentrated HCl solution (0.04 mL, 0.45 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was diluted with water, and extracted with EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4, evaporated in vacuo, and purified by preparative HPLC to give Compound 78 (45 mg, yield 23%). 1H NMR (DMSO-d6 300 MHz): δ 10.22 (s, 1H), 8.61 (s, 1H), 7.47 (s, 1H), 7.34-7.29 (m, 2H), 7.15-7.13 (m, 1H), 7.09-7.06 (m, 3H), 6.99 (s, 1H), 6.87-6.83 (m, 3H), 5.02 (d, J=2.4 Hz, 1H), 3.92 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H); MS (ESI): m/z 438.0[M+1]+.

후처리

  1. temperaturewas refluxed overnight
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. customevaporated in vacuo
  7. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-c3e5cde4ef48448fad48f7e6d036d92b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283229B2

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