Methanol → N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

HRID 2161ノート

反応式

HRID 2161 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:33]O>>[CH3:33][O:2][C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)=[O:3]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 19689579N-[3-carboxy-phenyl]-4-(2-(3-hydroxy-propyl-amino)-4-pyridyl)-2-pyrimidineamine

生成物 1

HCID 19689556N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

実験手順

2.0 g (5.4 mmol) of N-[3-carboxy-phenyl]-4-(2-(3-hydroxy-propyl-amino)-4-pyridyl)-2-pyrimidineamine and 0.28 ml (5.4 mmol) of conc. sulfuric acid are boiled under RF in 150 ml of methanol for 24 h. After cooling to RT, the reaction mixture is concentrated to half the volume, diluted with 100 ml of ethyl acetate and extracted twice with 50 ml of buffer (pH 7) each time. The organic phase is dried (Na2SO4) and concentrated. Crystallisation (methylene chloride/methanol) gives N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine; m.p. 162°-163°, FAB-MS: 380 (M+ +H).

後処理

  1. concentrationthe reaction mixture is concentrated to half the volume
  2. additiondiluted with 100 ml of ethyl acetate
  3. extractionextracted twice with 50 ml of buffer (pH 7) each time
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. concentrationconcentrated
  6. customCrystallisation (methylene chloride/methanol)

出典と根拠

ORDレコード
ord-4d75cb7565874f338140d42a8ca396c2
出典データセット
uspto-grants-1998_03
特許番号
US05728708

反応ノート

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