4,6-Dichloropyrimidine → HCID 59613383, compound

HRID 556786Notes

Reaction equation

HRID 556786 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[Na+].[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:14][C:15]1[N:16]=[CH:17][N:18]=[C:19]([NH:1][C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)[CH:20]=1

Participants

6

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 78747AminopyrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 59613383HCID 59613383, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-aminopyrazine (230 mg, 2.42 mmol), sodium tert-butoxide (232 mg, 2.42 mmol) and bis(tri-t-butylphosphine)palladium(0) (51 mg, 0.1 mmol) in toluene (2 mL) was degassed under a stream of nitrogen over 10 min. 4,6-Dichloropyrimidine (300 mg, 2.01 mmol) was added to the mixture and the reaction was heated at 80° C. for 2 h. After cooling, the solution was passed through a PS-SH cartridge and the solvent removed in vacuo. The residue was triturated with dichloromethane and the resulting solid was collected and dried by vacuum filtration to give crude 6-chloro-N-(pyrazin-2-yl)pyrimidin-4-amine (333 mg) which was used without further purification.

Workup

  1. customwas degassed under a stream of nitrogen over 10 min
  2. temperatureAfter cooling
  3. customthe solvent removed in vacuo
  4. customThe residue was triturated with dichloromethane
  5. customthe resulting solid was collected
  6. customdried by vacuum filtration

Sources & evidence

ORD record
ord-d4d6fd4f5d484e488db4b287edad0031
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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