Sodium hydride → HCID 59540559, compound

HRID 1677362Notes

Reaction equation

HRID 1677362 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:13]=2)[NH:8][C:7]=1[CH3:27])=[O:5])[CH3:2].[H-].[Na+].Cl[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[N:13]=2)[N:8]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:7]=1[CH3:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 59540809HCID 59540809, compound

Product 1

HCID 59540559HCID 59540559, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester (108 mg) in 3 ml of DMF was added 60% NaH. After stirring 15 minutes, (2-Chloromethoxy-ethyl)-trimethyl-silane (108 mg) was added and the mixture stirred at rt for 14 h. The mixture was partitioned between water and diethylether. The organic phase was concentrated and purified by flash chromatography (9:1 Hexanes:Ethyl acetate). Obtain 110 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ethyl ester.

Workup

  1. stirringthe mixture stirred at rt for 14 h
  2. customThe mixture was partitioned between water and diethylether
  3. concentrationThe organic phase was concentrated
  4. custompurified by flash chromatography (9:1 Hexanes:Ethyl acetate)

Sources & evidence

ORD record
ord-f96353e12c4649f39495e098751589bc
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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