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

HRID 1053197노트

반응식

HRID 1053197 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-498b6879bde441f49e84f45c6d5d255a
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09393246B2

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