tert-Butanol → HCID 24273408, compound

HRID 588404Notes

Reaction equation

HRID 588404 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[N:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1.[BH4-].[Na+].CC(O)(C)C>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[NH2:8])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 73172PyrazinecarbonitrileHCID 4311764Sodium borohydrideHCID 178478191HCID 178478191, compound

Product 1

HCID 24273408HCID 24273408, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Pyrazine-2-carbonitrile (10.5 g, 100 mmol) was dissolved in PhMe (100 mL) at 0° C. and 4-chlorophenyl magnesium bromide (100 ml, 1.0 M in Et2O, 100 mmol) was added portion-wise over 5 min. The reaction mixture was stirred for 6 h and NaBH4 (7.58 g, 201 mmol) and tBuOH (100 mL) were added. The reaction mixture was warmed to 60° C. for 18 h and quenched with 1 M aq NaOH solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (DCM:EtOH:NH3 200:8:1 to 50:8:1) to give the title compound as a brown oil (7.46 g, 34%). MS (ESI+) m/z=220.0 (M+H)+.

Workup

  1. customquenched with 1 M aq NaOH solution
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (DCM:EtOH:NH3 200:8:1 to 50:8:1)

Sources & evidence

ORD record
ord-1aea35ae2300462f92f81a08ea9d80c2
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Reaction notes

Loading…