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Ammonia → 2-{4-[3-(N,N-Dimethyl)amino-2-hydroxypropoxy]anilino}-4-(N-(n-butyl)anilino)pyrimidine

HRID 347739
노트
인쇄 미리보기

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HRID 347739 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:15][CH2:16][CH2:17][CH3:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl.Cl.[CH3:21][N:22]([CH2:24][CH:25]([OH:35])[CH2:26][O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)[CH3:23].CO.N>C(O)CCC>[CH3:23][N:22]([CH2:24][CH:25]([OH:35])[CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([NH:32][C:2]2[N:7]=[C:6]([N:8]([CH2:15][CH2:16][CH2:17][CH3:18])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:33][CH:34]=1)[CH3:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 887MethanolHCID 180091401-(4-Aminophenoxy)-3-(dimethylamino)propan-2-ol;dihydrochlorideHCID 210837462-Chloro-4-(N-(n-butyl)anilino)pyrimidine

생성물 1

HCID 210837322-{4-[3-(N,N-Dimethyl)amino-2-hydroxypropoxy]anilino}-4-(N-(n-butyl)anilino)pyrimidine수율 15.2%

시약·촉매·용매 1

HCID 263
1-Butanol
용매

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온도
95 °C

실험 절차

2-Chloro-4-(N-(n-butyl)anilino)pyrimidine (570 mg, 2.18 mmol) was dissolved in n-butanol (4 ml) and 4-[3-(N,N-dimethyl)amino-2-hydroxypropoxy]aniline dihydrochloride (Reference Example D-1; 554 mg, 1.97 mmol) was added. The resulting suspension was treated with methanol until all the solid dissolved. The reaction mixture was heated at 95° C. for 12 hours and allowed to cool to ambient temperature. The reaction mixture was then basified to pH 9–10 using methanolic ammonia and then evaporated onto silica (5 ml). The residue was purified by column chromatography eluting with methanol (15%):DCM:aqueous ammonia (1%). The resulting gum was re-evaporated from EtOAc twice to give the title product as a foam (130 mg).

후처리

  1. dissolutiondissolved
  2. temperatureto cool to ambient temperature
  3. customevaporated onto silica (5 ml)
  4. customThe residue was purified by column chromatography
  5. washeluting with methanol (15%)
  6. customThe resulting gum was re-evaporated from EtOAc twice

출처 및 근거

ORD 기록
ord-24fe94f779e14d0ab448bf6a97c55373
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176212B2

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