Phenyl chloroformate → HCID 68274511, compound

HRID 628986Notes

Reaction equation

HRID 628986 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]([O:13][C:14]([C:16]1[C:21]([O:22][CH2:23][CH3:24])=[C:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:19]=[C:18]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[N:17]=1)=[O:15])[CH3:12]>CC(=O)OCC>[CH2:11]([O:13][C:14]([C:16]1[C:21]([O:22][CH2:23][CH3:24])=[C:20]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[N:19]=[C:18]([C:31]2[CH:32]=[CH:33][C:34]([NH:37][C:2]([O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:3])=[CH:35][CH:36]=2)[N:17]=1)=[O:15])[CH3:12]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 67295455HCID 67295455, compound

Product 1

HCID 68274511HCID 68274511, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phenyl chloroformate (0.95 ml, 1.5 eq.) was added to a stirred solution of 2-(4-Amino-phenyl)-5-ethoxy-6-morpholin-4-yl-pyrimidine-4-carboxylic acid ethyl ester (1.15 g, 1 eq.) in EA (20 ml) and NaHCO3(sat) (20 ml). The mixture was reacted at room temperature for 2 hrs. The reaction mixture was diluted with NaHCO3(sat) and extracted with EA. The organic solution was washed with brine, was dried (MgSO4), filtered and concentrated under reduced pressure to give a crude carbamate (1.21 g, 80%).

Workup

  1. customThe mixture was reacted at room temperature for 2 hrs
  2. extractionextracted with EA
  3. washThe organic solution was washed with brine
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfb3bbe3a4de4c1b89f6aafa958760c6
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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