Hydrochloric Acid → 6-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-trifluoromethylphenyl)-pyrimidine-2,4-diamine

HRID 28532

反応式

HRID 28532 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][CH3:16])[N:5]=[C:4]([NH2:17])[N:3]=1.Cl.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>C(O)C.O1CCOCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:6]2[N:5]=[C:4]([NH2:17])[N:3]=[C:2]([NH:25][C:24]3[CH:26]=[CH:27][C:21]([C:20]([F:19])([F:28])[F:29])=[CH:22][CH:23]=3)[CH:7]=2)[CH:13]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 860043134-Chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2-yl-amine

生成物 1

HCID 112579346-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-trifluoromethylphenyl)-pyrimidine-2,4-diamine

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-methoxy-phenyl)-pyrimidin-2-yl-amine (0.050 g, 0.185 mmol) in ethanol (7.5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.03 ml) followed by 4-(trifluoromethyl)aniline (0.06 g, 0.37 mmol). The mixture was stirred under reflux for 45 minutes. After evaporation of volatiles under reduced pressure, the residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred for 30 min. Filtration provided the hydrochloride salt of the title compound which was dissolved in methanol (10 ml). A solution of sodium carbonate in water (1.0 M, 1 ml) was added. After stirring for 1 hour, volatiles were evaporated under reduced pressure. The crude product was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.053 g, 74% yield) as a white powder. 1H NMR (DMSO-d6) δ 3.90 (s, 3H, CH3), 6.44 (s, 2H, NH2), 6.81 (s, 1H, Ar), 7.19 (d, 1H, J=8.8 Hz, Ar), 7.46 (dd, 1H, J=8.8 Hz, J=2.6 Hz, Ar), 7.61 (d, 2H, J=8.5 Hz, Ar), 7.94 (d, 1H, J=2.6 Hz, Ar), 7.26 (d, 2H, J=8.5 Hz, Ar), 9.63 (s, 1H, NH).

後処理

  1. temperatureunder reflux for 45 minutes
  2. customAfter evaporation of volatiles under reduced pressure
  3. additionthe residue was treated with 1.0 M hydrochloric acid (10 ml)
  4. stirringstirred for 30 min
  5. filtrationFiltration

出典と根拠

ORDレコード
ord-155c05f946a844fda30246b2dd3a8057
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

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