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

HRID 986919노트

반응식

HRID 986919 반응식
[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

참가 물질

5

반응물 3

HCID 978031-(4-Chlorophenyl)ethylamineHCID 31358492-(4-Fluorophenoxy)ethanamineHCID 59099930(S)-6-chloro-N-(1-phenylethyl)pyrimidin-4-amine2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0d2131bd6319402d9a73650d15f5141e
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630469B2

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