4,6-Dichloropyrimidine → HCID 56926364, compound

HRID 384625Notes

Reaction equation

HRID 384625 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[N:14][C:13]([C:16]#[N:17])=[CH:12][N:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[N:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 2733832Lithium HexamethyldisilazideHCID 139252945-Aminopyrazine-2-carbonitrile

Product 1

HCID 56926364HCID 56926364, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
135 °C

Procedure

A mixture of 4,6-dichloropyrimidine (1.00 g, 6.7 mmol), 2-amino-5-cyanopyrazine (806 mg, 6.7 mmol) and bis(triphenylphosphine)palladium (II) chloride (94 mg, 0.134 mmol) in dry THF (24 mL) was degassed under a stream of nitrogen gas for 10 minutes with stirring. Lithium bis(trimethylsilyl)amide in THF (1M, 7.38 mL, 7.4 mmol) was added and the mixture was heated at 135° C. for 20 minutes using microwave irradiation. The reaction mixture was adsorbed onto silica and purified by flash column chromatography, eluting with 30% ethyl acetate in hexane, to give 5-(6-chloropyrimidin-4-ylamino)pyrazine-2-carbonitrile (300 mg, 19%).

Workup

  1. customwas degassed under a stream of nitrogen gas for 10 minutes
  2. custommicrowave irradiation
  3. custompurified by flash column chromatography
  4. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-28321370f6c7408a94bc3ce0b97073c3
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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