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

HRID 28570

反応式

HRID 28570 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-301de6b75a4347db8f7b5bd153a9d486
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

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