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Sodium Hydroxide → 4-Chloro-6-(1H-5-indolyloxy)-2-pyrimidinamine

HRID 2264598
ノート
印刷プレビュー

反応式

HRID 2264598 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[OH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2.[OH-].[Na+].CCOC(C)=O.CCCCCC>CC(C)=O.O>[NH2:1][C:2]1[N:3]=[C:4]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:5]=[C:6]([Cl:8])[N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 160545-HydroxyindoleHCID 655222-Amino-4,6-dichloropyrimidineHCID 21226206Ethyl acetate hexane

生成物 1

HCID 219493934-Chloro-6-(1H-5-indolyloxy)-2-pyrimidinamine

試薬・触媒・溶媒 2

HCID 180Acetone溶媒
HCID 962
Water
溶媒

反応条件

温度
70 °C

実験手順

10 g (61 mMol) 2-amino-4,6-dichloro-pyrimidine and 8.1 g (61 mMol) 5-hydroxyindole are suspended in 250 ml acetone. Then 120 ml 1 N NaOH in water are added and the mixture is stirred at an oilbath temperature of 70° C. for 2 h. The reaction mixture is partially concentrated and the residue diluted with water. Extraction with 3 portions of EtOAc, washing the organic layers twice with water and brine, drying (Na2SO4), addition of 100 g SiO2 and concentration in vacuo gives a powder. This is put on top of a chromatography column (SiO2; EtOAc/hexane 3:7) and eluted with EtOAc/hexane 3:7. Crystallization from hexane gives the title compound: m.p.: 192° C.; MS: [M+1]+=261; HPLC: AtRet=12.4.

後処理

  1. concentrationThe reaction mixture is partially concentrated
  2. additionthe residue diluted with water
  3. extractionExtraction with 3 portions of EtOAc
  4. washwashing the organic layers twice with water and brine
  5. customdrying
  6. addition(Na2SO4), addition of 100 g SiO2 and concentration in vacuo
  7. customgives a powder
  8. washeluted with EtOAc/hexane 3:7
  9. customCrystallization from hexane

出典と根拠

ORDレコード
ord-c5b770765eb7434e9e4b00bbbf28a74b
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07855215B2

反応ノート

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