Acetonitrile → 2-Chloro-4-(5-methylthiophen-2-yl)pyrimidine

HRID 507580

반응식

HRID 507580 반응식
[CH3:1][C:2]1[S:6][C:5](B(O)O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+].CC#N>C(Cl)Cl.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:10][C:11]1[N:16]=[C:15]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:14]=[CH:13][N:12]=1

참가 물질

8

반응물 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 2734374(5-Methylthiophen-2-yl)boronic acid

생성물 1

HCID 574288352-Chloro-4-(5-methylthiophen-2-yl)pyrimidine

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

A solution of 0.20 g (1.4 mmol) of 5-methyl-2-thiopheneboronic acid, 0.21 g (1.4 mmol) of 2,4-dichloropyrimidine and 49 mg (0.070 mmol) of bis(triphenylphosphine)palladium(II) chloride in 2 mL of a 2 M Na2CO3 aqueous solution and 5 mL of MeCN was heated in a microwave for 10 min at 160° C., then cooled to rt, diluted with CH2Cl2 and MeOH, and dried over MgSO4. The organic solvent was removed in vacuo, and the resulting solid was purified by flash chromatography eluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 211.

후처리

  1. dry with materialdried over MgSO4
  2. customThe organic solvent was removed in vacuo
  3. customthe resulting solid was purified by flash chromatography
  4. washeluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc

출처 및 근거

ORD 기록
ord-5b943c080c274e139a25b9d55fb6c580
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

연결된 노트

불러오는 중…