Dichloromethane → HCID 178433069、化合物

HRID 635654ノート

反応式

HRID 635654 の反応式
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24][N:25]([CH3:27])[CH3:26].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[CH3:26][N:25]([CH3:27])[CH2:24][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][N:18]1[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2[C:3]=1[N:11]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=2

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 252484N-(2-Piperidylmethyl)-dimethylamineHCID 178432852HCID 178432852、化合物

生成物 1

HCID 178433069HCID 178433069、化合物収率 34.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
140 °C

実験手順

To a mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (88.3 mg, 0.36 mmol) and N-(2-piperidylmethyl)-dimethylamine (Salor Chemical Company) (0.25 g, 1.72 mmol) was added a solution of K2CO3 (0.25 g, 1.60 mmol) in H2O (2.5 mL). This mixture was stirred at 140° C. in a closed-capped Wheaton vial for 2.5 h. After cooling, CH2Cl2 (10 ML) and H2O (10 mL) were added. The organic solution was removed and the aqueous solution was washed with CH2Cl2 (10 mL). The combined organic solutions were washed with saturated NaCl (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel) to give 43 mg (34%) of the title compound as a yellow oil. MS m/z: 350 (M+1), 305, 214. 1H NMR (DMSO-d6; 400 MHz): δ 1.63 (m, 6), 2.29 (s, 6), 2.40 (s, 3), 2.81 (m, 2), 3.03 (br t, 1, J=11.8), 4.53-4.63 (m, 2), 6.75 (s, 1), 7.37 (m, 1), 7.50 (t, 2, J=7.5), 7.81 (d, 2, J=7.8), 12.47 (s, 1).

後処理

  1. temperatureAfter cooling
  2. customThe organic solution was removed
  3. washthe aqueous solution was washed with CH2Cl2 (10 mL)
  4. washThe combined organic solutions were washed with saturated NaCl (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel)

出典と根拠

ORDレコード
ord-3b59129dae404b18b1c97d5394c1106b
出典データセット
uspto-grants-2001_02
特許番号
US06187777B1

反応ノート

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