Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-(prop-1-en-2-yl)pyrazine-2-carboxylate → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-isopropylpyrazine-2-carboxylate

HRID 467632Notes

Reaction equation

HRID 467632 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][C:12]([C:15]([CH3:17])=[CH2:16])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:25]([O:24][C:22]([N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:13][N:14]=1)=[O:23])([CH3:26])([CH3:27])[CH3:28]

Participants

4

Reactant 1

HCID 70097498Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-(prop-1-en-2-yl)pyrazine-2-carboxylate

Product 1

HCID 70097991Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-isopropylpyrazine-2-carboxylateYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 3-(bis(tert-butoxycarbonyl)amino)-6-(prop-1-en-2-yl)pyrazine-2-carboxylate (323 mg, 0.82 mmol) in MeOH (4 ml) was charged under an argon atmosphere at r.t. with Pd/C 10% (30 mg, 0.28 mmol). The reaction mixture was stirred at r.t. under a hydrogen atmosphere for 15 h, filtrated and the solvent was removed to yield the product as yellow viscous oil (302 mg, 92%) which was used without any purification.

Workup

  1. filtrationfiltrated
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-cf095d0f8be54f33bf3f50a08e3ee04e
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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