Dimethylformamide → HCID 59852844、化合物

HRID 1670209ノート

反応式

HRID 1670209 の反応式
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O.C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:2]2[N:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=3[F:18])[CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 59853046HCID 59853046、化合物

生成物 1

HCID 59852844HCID 59852844、化合物収率 30.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-chloro-4-(2-fluoro-4-nitrophenoxy)pyrimidine (0.66 g, 2.44 mmol), 4-methoxybenzylamine (0.34 g, 3.45 mmol), K2CO3 (0.37 g, 2.66 mmol), and DMF (15 mL) was heated at 100° C. for 1 h. The mixture was cooled, diluted with H2O (100 mL) and extracted with EtOAc (100 mL). The organic phase was washed twice each with saturated NaHCO3 solution and brine. The organics were dried (MgSO4) and concentrated to give the crude product. Flash chromatography on SiO2 using 1-3% MeOH in CH2Cl2 as the eluent gave the title compound (275 mg, 29%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 8.40-8.21 (m, 2H), 8.16 (dd, 1H, J=8.8, 1.7 Hz), 7.98 (br s, 0.5H), 7.73-7.55 (m, 1.5H), 7.16 (br s, 1H), 6.85-6.71 (m, 3H), 6.37 (s, 1H), 4.43 (br s, 1H), 3.95 (br s, 1H), 3.69 (s, 3H).

後処理

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic phase was washed twice each with saturated NaHCO3 solution and brine
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude product

出典と根拠

ORDレコード
ord-1f1007ae54a94714b30f7ad6c20b779c
出典データセット
uspto-grants-2011_08
特許番号
US07989477B2

反応ノート

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