Sodium hydride → Tert-butyl ethyl (5-nitropyrazin-2-yl)propanedioate

HRID 1502114Notes

Reaction equation

HRID 1502114 reaction equation
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[C:17]1[CH:22]=[N:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1>CN(C=O)C.CCOC(C)=O>[N+:23]([C:20]1[N:21]=[CH:22][C:17]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[N:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 140869592-Bromo-5-nitropyrazine

Product 1

HCID 86693017Tert-butyl ethyl (5-nitropyrazin-2-yl)propanedioate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of NaH (60%, 3.0 g, 75 mmol) in 100 mL of DMF was added tert-butyl ethyl propanedioate (14.1 g, 75 mmol) dropwise at 25° C. The mixture was stirred at 40° C. for 30 minutes and 2-bromo-5-nitropyrazine (10.2 g, 50 mmol) in 50 mL of DMF was added dropwise. The resulting suspension was stirred at 50° C. for 2 hours and diluted with 500 mL of EtOAc. The mixture was washed with water (100 mL*3), brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (petrol ether: EtOAc=5:1) to afford title compound.

Workup

  1. stirringThe resulting suspension was stirred at 50° C. for 2 hours
  2. washThe mixture was washed with water (100 mL*3), brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (petrol ether: EtOAc=5:1)

Sources & evidence

ORD record
ord-91bd834719c74fbc83d9a0ce92727e8a
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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