Water → HCID 70570800, compound

HRID 2403602Notes

Reaction equation

HRID 2403602 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]([CH:35]=[CH:36][CH:37]=2)[CH2:21][N:22]([CH3:34])[C:23](=[O:33])[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:14][N:13]=1.O>CN(C=O)C>[C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][C:23]([N:22]([CH3:34])[CH2:21][C:20]1[CH:35]=[CH:36][CH:37]=[C:18]([C:15]2[CH:16]=[N:17][C:12]([O:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[N:13][CH:14]=2)[CH:19]=1)=[O:33])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 86667972HCID 86667972, compound

Product 1

HCID 70570800HCID 70570800, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridin-4-ylmethanol (112 mg) was dissolved in DMF (4 ml), and NaH (45 mg) was added thereto under ice-cooling. After stirring at the same temperature for 30 minutes, tert-butyl (2-{[3-(2-chloropyrimidin-5-yl)benzyl](methyl)amino}-2-oxoethyl)carbamate (200 mg) was added thereto, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (0% to 7% MeOH/CHCl3) to obtain tert-butyl[2-(methyl{3-[2-(pyridin-4-ylmethoxy)pyrimidin-5-yl]benzyl}amino)-2-oxoethyl]carbamate (237 mg).

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring at room temperature for 2 hours
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (0% to 7% MeOH/CHCl3)

Sources & evidence

ORD record
ord-d16cf80a3acb43fda2eeb9f9d3dbc03e
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

Loading…