Ethyl chloroformate → ethyl pyrido[3,4-b]pyrazine-6(5H)-carboxylate

HRID 1713138Notes

Reaction equation

HRID 1713138 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]=12.Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Li+].[BH4-]>C1COCC1>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[CH2:7][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:10][C:2]=12

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 638007Pyrido[3,4-b]pyrazineHCID 4148881Lithium borohydride

Product 1

HCID 57420579ethyl pyrido[3,4-b]pyrazine-6(5H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

A solution of pyrido[3,4-b]pyrazine (20.0 g, 153 mmol) in anhydrous THF (250 mL) is cooled to −25° C. A solution of ethyl chloroformate (17.5 ml, 183 mmol) in THF (46 mL) is added dropwise. The mixture is stirred 1 hr at −25° C., and then LiBH4 (2.0 M, 23 mL, 46 mmol) is added dropwise and the mixture is stirred for 1 hr. The reaction is quenched with the addition of 1N NaOH (100 mL) and extracted with Et2O (3×100 mL). The organic extractions are combined, dried and evaporated. The crude product is purified by silica gel column chromatography eluting with hexane/EtOAc (3:2) to yield the title compound. MS (+VE) m/z 206.14 (M++1).

Workup

  1. stirringthe mixture is stirred for 1 hr
  2. customThe reaction is quenched with the addition of 1N NaOH (100 mL)
  3. extractionextracted with Et2O (3×100 mL)
  4. extractionThe organic extractions
  5. customdried
  6. customevaporated
  7. customThe crude product is purified by silica gel column chromatography
  8. washeluting with hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-969e6482245a47d1a619dc16993fd405
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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