3-Nitrophenylboronic Acid → 2-Chloro-4-(3-nitrophenyl)pyrimidine

HRID 14976

반응식

HRID 14976 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10]>>[Cl:1][C:2]1[N:7]=[C:6]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:17]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

3

반응물 2

HCID 16773-Nitrophenylboronic AcidHCID 775312,4-Dichloropyrimidine

생성물 1

HCID 249018872-Chloro-4-(3-nitrophenyl)pyrimidine수율 60%

실험 절차

2,4 dichloropyrimidine was coupled to 3-nitrophenyl boronic acid following procedure A. The workup and purification protocol was modified as follows: The THF was removed from the reaction mixture by rotary evaporation and the residue taken up in ethyl acetate. The solution was washed with water followed by sat. NaCl and the organic layer concentrated by rotary evaporation until the product started to precipitate, at which point the flask was placed in an ice bath for two hours. The product was collected by filtration in a Buchner funnel. The yield was 60%. Product was >95% pure by LC-MS and showed the expected M+H+ of 236.

후처리

  1. customThe workup and purification protocol
  2. customThe THF was removed from the reaction mixture by rotary evaporation
  3. washThe solution was washed with water
  4. concentrationthe organic layer concentrated by rotary evaporation until the product
  5. customto precipitate, at which point the flask
  6. filtrationThe product was collected by filtration in a Buchner funnel

출처 및 근거

ORD 기록
ord-43dabcc19e814c72b996c7b0f947aae1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732444B2

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