Potassium Phosphate, Tribasic → 6-Cyclopropylpyrazine-2-carbonitrile

HRID 931106Notes

Reaction equation

HRID 931106 reaction equation
[C:1]([C:3]1[N:8]=[C:7](Cl)[CH:6]=[N:5][CH:4]=1)#[N:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:18]1(B(O)O)[CH2:20][CH2:19]1>O1CCCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:18]1([C:7]2[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[N:5][CH:6]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 813036-Chloropyrazine-2-carbonitrileHCID 2760897Cyclopropylboronic acid

Product 1

HCID 898540196-Cyclopropylpyrazine-2-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 6-cyano-2-chloropyrazine (0.3 g, 2.1 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium (II) (153.6 mg, 0.21 mmol), potassium phosphate (1.3 g, 6.30 mmol) and cyclopropylboronic acid (0.184 mg, 2.1 mmol) in tetrahydrofuran (25 mL, nitrogen bubbled) was degassed for 15 min. using nitrogen. The reaction mixture was refluxed for 16 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 5-20% ethyl acetate in petroleum ether) to afford 6-cyclopropylpyrazine-2-carbonitrile (250 mg, 50%).

Workup

  1. customwas degassed for 15 min.
  2. temperatureThe reaction mixture was refluxed for 16 h
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 5-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-7e58671c7e634fc59eccd174092cac15
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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