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

HRID 28535노트

반응식

HRID 28535 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78222b70b6db43e0874041f8d1b94b87
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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