Carbon Dioxide → tert-Butyl pyrazin-2-ylcarbamate

HRID 8180Notes

Reaction equation

HRID 8180 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.C(=O)=O>CO>[C:1]([O:5][C:6]([NH:8][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 14798Sodium HydroxideHCID 22014485Di-(t-butoxycarbonyl)aminopyrazine

Product 1

HCID 21992941tert-Butyl pyrazin-2-ylcarbamateYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Di-(t-butoxycarbonyl)aminopyrazine (2.1 g, 7.1 mM) in methanol (50 ml) under nitrogen, was treated with aqueous sodium hydroxide (2.5 M, 2.84 ml, 7.1 mM), and stirred at ambient temperature for 2 hours. The mixture was neutralised by the addition of water (25 ml) and solid carbon dioxide, then methanol evaporated. The residual aqueous solution was extracted with dichloromethane (2×20 ml), the extracts washed with brine (20 ml) and evaporated. The resulting solid was triturated with isohexane (50 ml) to give the title product as a white solid (1.03 g).

Workup

  1. custommethanol evaporated
  2. extractionThe residual aqueous solution was extracted with dichloromethane (2×20 ml)
  3. washthe extracts washed with brine (20 ml)
  4. customevaporated
  5. customThe resulting solid was triturated with isohexane (50 ml)

Sources & evidence

ORD record
ord-5ffcee3aef244c46ad73a59445cc6d99
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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