Hydrochloric Acid → 6-(5-Chloro-2-ethoxy-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine

HRID 28570

반응식

HRID 28570 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][CH2:16][CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=1.Cl.[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1>C(O)C.O1CCOCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:16][CH3:17])=[C:8]([C:6]2[N:5]=[C:4]([NH2:18])[N:3]=[C:2]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=3)[CH:7]=2)[CH:13]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 860043254-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

생성물 1

HCID 111990476-(5-Chloro-2-ethoxy-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine수율 53.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred suspension of 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (0.030 g, 0.106 mmol) in ethanol (5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.015 ml) followed by p-tolylamine (0.014 g, 0.127 mmol). After heating under reflux for 3.5 hours, the volatiles were evaporated under reduced pressure. The residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred overnight. After filtration, the solid was dissolved in methanol (10 ml) and treated with aqueous sodium carbonate solution (1.0 M, 1 ml). After stirring for 0.5 hours, the volatiles were evaporated under reduced pressure, the solid was stirred with water (10 ml) for 15 minutes, and filtered to provide the title compound (0.020 g, 53% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.37 (t, 3H, J=6.8 Hz, CH3), 2.27 (s, 3H, CH3), 4.12 (q, 2H, J=6.6 Hz, CH2), 6.25 (s, 2H, NH2), 6.75 (s, 1H, Ar), 7.10-7.14 (m, 3H, Ar), 7.40-7.42 (m, 1H, Ar), 7.55 (d, 2H, J=8.0 Hz, Ar), 7.92 (s, 1H, Ar), 9.05 (s, 1H, NH).

후처리

  1. temperatureAfter heating
  2. temperatureunder reflux for 3.5 hours
  3. customthe volatiles were evaporated under reduced pressure
  4. additionThe residue was treated with 1.0 M hydrochloric acid (10 ml)
  5. filtrationAfter filtration
  6. dissolutionthe solid was dissolved in methanol (10 ml)
  7. additiontreated with aqueous sodium carbonate solution (1.0 M, 1 ml)
  8. stirringAfter stirring for 0.5 hours
  9. customthe volatiles were evaporated under reduced pressure
  10. stirringthe solid was stirred with water (10 ml) for 15 minutes
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-301de6b75a4347db8f7b5bd153a9d486
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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