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

HRID 2267356Notes

Reaction equation

HRID 2267356 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-19d00f4dd2d54f4ba9a7c8abb486528f
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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