Methyl iodide → HCID 25099829, compound

HRID 2381985Notes

Reaction equation

HRID 2381985 reaction equation
C(OC(=O)[N:7]([N:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][O:30][CH3:31])[CH2:24][CH2:23]1)[C:8]([C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:14][CH:15]=1)=[O:9])(C)(C)C.[H-].[Na+].IC>CN(C=O)C>[CH3:31][O:30][CH2:29][CH2:28][N:25]1[CH2:24][CH2:23][N:22]([NH:7][C:8]([C:10]2[CH:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][CH:11]=2)=[O:9])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68557057HCID 68557057, compound

Product 1

HCID 25099829HCID 25099829, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(2-methoxy-ethyl)-piperazin-1-yl]-(2-phenyl-pyrimidine-5-carbonyl)-carbamic acid tert-butyl ester (0.21 mmol), NaH (60%, 0.66 mmol) and iodomethane (0.63 mmol) in DMF (8 mL) is stirred under N2 at rt overnight. The reaction mixture is quenched with water, and extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-2% methanol in DCM to afford 2-phenyl-pyrimidine-5-carboxylic acid [4-(2-methoxy-ethyl)-piperazin-1-yl]-amide (32 mg, 44%) as a solid. MS: 342 (M+H).

Workup

  1. customThe reaction mixture is quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer is separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 0-2% methanol in DCM

Sources & evidence

ORD record
ord-9d19b17481604ec68644f39da893c424
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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