Dimethylformamide → HCID 22248558, compound

HRID 890106Notes

Reaction equation

HRID 890106 reaction equation
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[C:16]([O:20][C:21]([NH:23][C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].CN([CH:33]=[O:34])C>O1CCCC1>[C:16]([O:20][C:21]([NH:23][C:24]1[C:29]([CH:33]=[O:34])=[N:28][CH:27]=[CH:26][N:25]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 21992941tert-Butyl pyrazin-2-ylcarbamateHCID 178418339Butyllithium

Product 1

HCID 22248558HCID 22248558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

After adding 4 ml of n-butyllithium (2.46 M, n-hexane solution) to a solution of 1.384 g of 2,2,6,6-tetramethylpiperidine in tetrahydrofuran (15 ml) at −20° C. under a nitrogen atmosphere, the mixture was stirred for 30 minutes while cooling on ice. The reaction mixture was cooled to −70° C., and then a solution of 800 mg of 2-(tert-butoxycarbonylamino)pyrazine in tetrahydrofuran (3 ml) was added dropwise, the mixture was stirred for 1 hour, 3 ml of N,N-dimethylformaldehyde was added, and stirring was continued for 30 minutes. After removing the cooling bath and stirring for 30 minutes, water was added and extraction was performed with ethyl acetate. The extract was dried and concentrated and then purified by silica gel column chromatography (solvent: ethyl acetate/n-hexane) to obtain 72 mg of crude 2-(tert-butoxycarbonylamino)pyrazine-3-carboxaldehyde.

Workup

  1. temperaturewhile cooling on ice
  2. stirringthe mixture was stirred for 1 hour
  3. stirringstirring
  4. waitwas continued for 30 minutes
  5. customAfter removing the cooling bath
  6. stirringstirring for 30 minutes
  7. additionwater was added
  8. extractionextraction
  9. customThe extract was dried
  10. concentrationconcentrated
  11. custompurified by silica gel column chromatography (solvent: ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-5402654395fb4c13858d1df89e87e470
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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