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

HRID 507580ノート

反応式

HRID 507580 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5b943c080c274e139a25b9d55fb6c580
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

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