Isoamyl Nitrite → HCID 86660197, compound

HRID 2368354Notes

Reaction equation

HRID 2368354 reaction equation
N[C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[N:4][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[Br:15]C(Br)C.N(OCCC(C)C)=O.C[Si](C)(C)Br.C([O-])(O)=O.[Na+]>>[Br:15][C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[N:4][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:6][N:7]=1

Participants

6

Reactant 5

HCID 8053Isoamyl NitriteHCID 112011,1-DibromoethaneHCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 67299911HCID 67299911, compound

Product 1

HCID 86660197HCID 86660197, compound

Procedure

To a solution of methyl 3-amino-6-cyclopropylpyrazine-2-carboxylate (1 g, 5.18 mmol, intermediate A-10, step 2) in dibromethane (16.0 ml, 229 mmol) at 0° under an argon atmosphere was added isoamyl nitrite (1.49 ml, 11.1 mmol) and trimethylbromosilane (2.03 ml, 15.7 mmol). The mixture was stirred at 0° for 10 min and at r.t overnight. The reaction mixture was poured onto ice, neutralized with solid NaHCO3, extracted with dichloromethane, dried over MgSO4, filtered and evaporated. The title compound was obtained after silica gel chromatography using a heptane/ethylacetate gradient as viscous oil (450 mg, 34%).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-be98508376d04b5898437138a23c8583
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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