Phenyl chloroformate → HCID 67295418, compound

HRID 629019Notes

Reaction equation

HRID 629019 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH3:11][S:12][C:13]1[C:14]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[N:17][CH:18]=1.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:11][S:12][C:13]1[C:14]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:21][CH:20]=2)=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 67295403HCID 67295403, compound

Product 1

HCID 67295418HCID 67295418, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The phenyl chloroformate (0.84 ml, 6.68 mmole, 2.5 eq) was added to a mixture of 4-(5-(methylthio)-4morpholinopyrimidin-2-yl)benzeneamine (0.84 g, 2.18 mmole, 1 eq), NaHCO3(aq) (1M, 6.3 ml, 6.3 mmole 2.2 eq) and ACN (13 ml) at 0□. The reaction mixture was stirred for 8 hrs and then dried. The reaction mixture was partitioned between EA and water, the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 2:1) to give a yellow solid (80%).

Workup

  1. customdried
  2. customThe reaction mixture was partitioned between EA and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-6d17f00d434f4dcd95207c23f26fb8ee
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

Loading…