Phenyl chloroformate → [4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-carbamic acid phenyl ester

HRID 629013Notes

Reaction equation

HRID 629013 reaction equation
[Cl:1][C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[N:3]=1.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>CC(=O)OCC.C([O-])(O)=O.[Na+]>[C:27]1([O:26][C:24](=[O:25])[NH:22][C:19]2[CH:20]=[CH:21][C:16]([C:4]3[N:3]=[C:2]([Cl:1])[C:7]([S:8][CH3:9])=[C:6]([N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)[N:5]=3)=[CH:17][CH:18]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 86673495HCID 86673495, compound

Product 1

HCID 86673502[4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-carbamic acid phenyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (915 mg, 2.717 mmol.) in EA (20 ml) and NaHCO3 (20 ml) the reaction was stirred at r.t. then added dropwise to slurry of phenyl chloroformate (851 mg, 0.543 mmol, 2.0 eq) at reaction for 2 hr. The reaction mixture was partitioned between EA/NaHCO3, the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was recrystallized by (Hexane/EtOAc) to give a pale yellow product of 1056 mg (85.1%).

Workup

  1. additionthen added dropwise
  2. customThe reaction mixture was partitioned between EA/NaHCO3
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was recrystallized by (Hexane/EtOAc)
  8. customto give a pale yellow product of 1056 mg (85.1%)

Sources & evidence

ORD record
ord-6cd075b05e8646f29e86b821bca9660e
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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