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

HRID 924788

반응식

HRID 924788 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH:24]=O)[CH3:19].[NH2:33][C:34]([NH2:36])=[O:35].Cl>CCO.CO.CCOC(C)=O>[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:24]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:36][C:34](=[O:35])[NH:33]2)[CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH3:19]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-oneHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

생성물 1

HCID 668259394-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one수율 7.5%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-(4-methoxyphenyl)-2-phenylethanone (200 mg, 0.88 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (187 mg, 0.89 mmol), and urea (159 mg, 2.65 mmol) in anhydrous EtOH (20 mL) was added concentrated HCl solution (0.1 mL). The reaction mixture was refluxed for two days. When TLC (EtOAc:MeOH=10:1) showed that about 30% of the starting materials were consumed, the reaction mixture was concentrated. The residue was purified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC to afford Compound 20 as a yellow solid (30 mg, yield: 7.5%). 1H NMR (DMSO-d6 300 MHz): δ 10.30 (s, 1H), 8.65 (s, 1H), 7.52 (s, 1H), 7.45 (s, 1H), 7.20 (s, 1H), 7.09-7.15 (m, 2H), 6.96-7.08 (m, 3H), 6.75-6.82 (m, 4H), 5.12 (s, 1H), 4.00-4.10 (m, 2H), 3.70 (s, 3H), 1.34 (t, J=6.9 Hz, 3H); MS (ESI): m/z 462.0 [M+1]+.

후처리

  1. temperatureThe reaction mixture was refluxed for two days
  2. customwere consumed
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC

출처 및 근거

ORD 기록
ord-74d3cf915bfb43bca58dbc161beb9f6d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283229B2

연결된 노트

불러오는 중…