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

HRID 28535ノート

反応式

HRID 28535 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[N:13]=[C:12]([NH2:14])[N:11]=[C:10]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH:9]=2)[CH:7]=1.[Sn](Cl)Cl.Cl>CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:10]2[CH:9]=[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:25][CH3:26])[N:13]=[C:12]([NH2:14])[N:11]=2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 111646216-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-nitro-phenyl)-pyrimidine-2,4-diamine

生成物 1

HCID 11416581N*4*-(4-Amino-phenyl)-6-(5-chloro-2-methoxy-phenyl)-pyrimidine-2,4-diamine収率 64%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of the title compound of Example 11 (0.060 g, 0.16 mmol) and tin (II) chloride (0.19 g, 1.0 mmol) in a solution of 1.0 M hydrochloric acid and methanol (1:10, 15 ml) was heated under reflux for 2 hours. After evaporation of volatiles under reduced pressure, the residue was treated with aqueous sodium hydroxide solution (1.0 M, 10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.035 g, 64% yield) as a white powder. 1H NMR (DMSO-d6) δ 3.84 (s, 3H, CH3), 4.83 (s, 2H, NH2), 6.08 (s, 2H, NH2), 6.54 (d, 2H, J=8.7 Hz, Ar), 6.58 (s, 1H, Ar), 7.13 (d, 1H, J=8.9 Hz, Ar), 7.25 (d, 2H, J=8.7 Hz, Ar), 7.41 (dd, 1H, J=8.9 Hz, J-2.8 Hz, Ar), 7.89 (d, 1H, J=2.8 Hz, Ar), 8.67 (s, 1H, NH).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of volatiles under reduced pressure
  4. additionthe residue was treated with aqueous sodium hydroxide solution (1.0 M, 10 ml)
  5. filtrationFiltration

出典と根拠

ORDレコード
ord-78222b70b6db43e0874041f8d1b94b87
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

反応ノート

読み込み中…