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

HRID 1181360ノート

反応式

HRID 1181360 の反応式
[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

参加物

5

反応物 3

HCID 996PhenolHCID 693735413-Fluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidineHCID 178499302HCID 178499302、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
200 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ad5c54edae6149c9b80d02527d8b2dc4
出典データセット
uspto-grants-2007_10
特許番号
US07285557B2

反応ノート

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