Phenol → 6-(4-chlorophenyl)-3-{4-[2-(3-fluoropyrrolidin-1-yl)ethoxy]-3-methoxyphenyl}thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1181360노트

반응식

HRID 1181360 반응식
[F:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[O:19][CH3:20])[CH2:3]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:32][C:31]([C:33](OC)=[O:34])=[C:30](/[N:37]=[CH:38]/N(C)C)[CH:29]=2)=[CH:24][CH:23]=1.C1(O)C=CC=CC=1>C(Cl)Cl>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[S:32][C:31]3[C:33](=[O:34])[N:16]([C:13]4[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:4]5[CH2:5][CH2:6][CH:2]([F:1])[CH2:3]5)=[C:11]([O:19][CH3:20])[CH:12]=4)[CH:38]=[N:37][C:30]=3[CH:29]=2)=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 693735413-Fluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidineHCID 178499302HCID 178499302, 화합물

생성물 1

HCID 101853586-(4-chlorophenyl)-3-{4-[2-(3-fluoropyrrolidin-1-yl)ethoxy]-3-methoxyphenyl}thieno[3,2-d]pyrimidin-4(3H)-one수율 11.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
200 °C

실험 절차

3-Fluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine (0.0442 g, 0.1740 mmol) and methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylidene]amino}thiophene-2-carboxylate (0.056 g, 0.1740 mmol) were charged to a flask. Phenol (1 g) was added and the reaction heated to 200° C. The reaction was stirred for 45 min until all starting material was gone. The mix was then cooled to RT, diluted with CH2Cl2 (30 mL) and washed with 1N NaOH (2×30 mL), water (1×30 mL), brine (1×30 mL), dried over MgSO4, filtered, and concentrated. The residue was purified on a chromatatron (98:2 CH2Cl2:MeOH) to give 0.010 g (0.020 mmol, 11%) of the product as a tan solid. 1H NMR (CDCl3) δ 8.13 (s, 1H), 7.65 (d, 2H, J=8.3 Hz), 7.52 (s, 1H), 7.43 (d, 2H, J=8.4 Hz), 7.00 (d, 1H, J=8.4 Hz), 6.93 (m, 2H), 5.29-5.13 (m,1H), 4.23 (t, 2H, J=5.7 Hz), 3.88 (s, 3H), 3.12-2.93 (m, 5H), 2.68 (bs, 1H), 2.25-2.06 (m, 2H).

후처리

  1. temperatureThe mix was then cooled to RT
  2. washwashed with 1N NaOH (2×30 mL), water (1×30 mL), brine (1×30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a chromatatron (98:2 CH2Cl2:MeOH)

출처 및 근거

ORD 기록
ord-ad5c54edae6149c9b80d02527d8b2dc4
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285557B2

반응 노트

불러오는 중…