1-(4-Chlorophenyl)ethylamine → N4-[2-(4-Fluorophenoxy)ethyl]-N6-[(1S)-(1-phenylethyl)]pyrimidine-4,6-diamine

HRID 986919ノート

反応式

HRID 986919 の反応式
[C:1]1([C@@H:7]([NH:9][C:10]2[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC(C(N)C)=CC=1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH2:34][NH2:35])=[CH:30][CH:29]=1>C(Cl)Cl>[F:27][C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH2:34][NH:35][C:14]2[CH:15]=[C:10]([NH:9][C@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:8])[N:11]=[CH:12][N:13]=2)=[CH:30][CH:29]=1

参加物

5

反応物 3

HCID 978031-(4-Chlorophenyl)ethylamineHCID 31358492-(4-Fluorophenoxy)ethanamineHCID 59099930(S)-6-chloro-N-(1-phenylethyl)pyrimidin-4-amine2 回

生成物 1

HCID 44393171N4-[2-(4-Fluorophenoxy)ethyl]-N6-[(1S)-(1-phenylethyl)]pyrimidine-4,6-diamine収率 54.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

4-[(1S)-(1-phenylethyl)amino]-6-chloropyrimidine, (Intermediate III, Compound of Example 6), (234 mg, 1.0 mmole) and [2-(4-fluorophenoxy)ethyl]amine (357 mg, 2.3 mmole) were combined in a 2 mL pressure vial which was then securely capped. The vial was heated at 150° C. for 20 hours. After cooling, the solid mass was dissolved in CH2Cl2 (25 mL) and extracted with saturated sodium carbonate (25 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from CH2Cl2 (5 mL) to afford the titled compound as a white solid (191 mg, 54%). 1H NMR (CDCl3) δ 1.54 (d, J=6.6 Hz, 3H), 3.54 (q, J=5.5 Hz, 2H), 3.94 (t, J=5.5 Hz, 2H), 4.59 (p, J=6.6 Hz, 1H), 5.05 (broad m, 1H), 5.08 (s, 1H), 5.34 (broad d,1H), 6.77 (m, 2H), 6.95 (t, J=9.1 Hz, 2H), 7.23 (m,1H), 7.32 (d, J=4.4 Hz, 4H), 8.09 (s, 1H), LC/MS (MH+) m/e 353.79 obs.

後処理

  1. customwas then securely capped
  2. temperatureAfter cooling
  3. extractionextracted with saturated sodium carbonate (25 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from CH2Cl2 (5 mL)

出典と根拠

ORDレコード
ord-0d2131bd6319402d9a73650d15f5141e
出典データセット
uspto-grants-2003_10
特許番号
US06630469B2

反応ノート

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