3-Chloro-4-fluoroaniline → N-(6-amino-pyridin-2-yl)-N'-(3-chloro-4-fluorophenyl)-pyrimidine-4,6-diamine

HRID 404777ノート

反応式

HRID 404777 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=2)[CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[F:24])[NH2:20]>C(O)CCC>[NH2:15][C:11]1[N:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:20][C:19]3[CH:21]=[CH:22][C:23]([F:24])=[C:17]([Cl:16])[CH:18]=3)[N:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 97083-Chloro-4-fluoroanilineHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

生成物 1

HCID 66769640N-(6-amino-pyridin-2-yl)-N'-(3-chloro-4-fluorophenyl)-pyrimidine-4,6-diamine収率 232.9%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

A mixture of N-(6-chloro-pyrimidin-4-yl)-pyridine-2,6-diamine (1.000 g, 4.512 mmol) and 3-chloro-4-fluoroaniline (1.380 mmol) in 10 mL of n-butanol in a sealed vial was heated at 120° C. for 24 h. The sample was cooled, was concentrated to remove most of the n-butanol, and was then diluted with EtOAc and sat. NaHCO3 solution. The sample was stirred at room temperature for 30 min and was filtered. The solid was washed with fresh EtOAc and water and vacuum dried to give 1.063 g of N-(6-amino-pyridin-2-yl)-N′-(3-chloro-4-fluorophenyl)-pyrimidine-4,6-diamine (Int-E) as tan solid. MS (ES) (m/z) 331/333 (M+1, 100/65%). TLC (SiO2, 10% MeOH in CHCl3): Rf 0.25.

後処理

  1. temperatureThe sample was cooled
  2. concentrationwas concentrated
  3. customto remove most of the n-butanol
  4. additionwas then diluted with EtOAc and sat. NaHCO3 solution
  5. filtrationwas filtered
  6. washThe solid was washed with fresh EtOAc and water and vacuum
  7. customdried

出典と根拠

ORDレコード
ord-bf9371de54d84360ae7a4564f63975a4
出典データセット
uspto-grants-2014_06
特許番号
US08748606B2

反応ノート

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