Sodium hydride → HCID 22105557, compound

HRID 1455991Notes

Reaction equation

HRID 1455991 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:22]([O:29][C:30]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][C:31]=1[CH2:32]Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([O:29][C:30]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][C:31]=1[CH2:32][N:8]([C:9]1[N:10]=[CH:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzeneHCID 22105664HCID 22105664, compound

Product 1

HCID 22105557HCID 22105557, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-(tert-butoxycarbonylamino)pyrazine-2-carboxylate (10.7 g 0.04 mol) in DMF (160 ml) at 20° C., under argon atmosphere, was added sodium hydride dispersion (50% in oil, 1.85 g, 0.04 mol) and stirred for 1 hour until effervescence ceased. Next was added 2-benzyloxy-5-bromobenzylbromide (14.3 g, 0.04 mol) and stirring continued at 20° C. under argon for 2 hours. The solvent was evaporated at reduced pressure and the residue partitioned between dichloromethane (500 ml) and water (250 ml), the organic layer was dried over magnesium sulphate and evaporated at reduced pressure to give a crude solid (21 g). Purification was by chromatography on silica, eluting with 5% ethyl acetate in dichloromethane to give ethyl 5-(N-(2-benzyloxy-5-bromobenzyl)-N-tert-butoxycarbonylamino)pyrazine-2-carboxylate as a white solid (16 g, mp 116°-7° C.).

Workup

  1. stirringstirring
  2. waitcontinued at 20° C. under argon for 2 hours
  3. customThe solvent was evaporated at reduced pressure
  4. customthe residue partitioned between dichloromethane (500 ml) and water (250 ml)
  5. dry with materialthe organic layer was dried over magnesium sulphate
  6. customevaporated at reduced pressure
  7. customto give a crude solid (21 g)
  8. customPurification
  9. washeluting with 5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-e1c98a2718534a76830c6d35bb456d7d
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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