Phenyl chloroformate → HCID 59509064, compound

HRID 1020079Notes

Reaction equation

HRID 1020079 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1.CCN(C(C)C)C(C)C.[NH2:35][C:36]1[CH:37]=[C:38]([CH2:42][C:43]([OH:45])=[O:44])[CH:39]=[CH:40][CH:41]=1>ClCCl.O1CCOCC1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:24]=[CH:23][N:22]=[C:21]([NH:25][C:2](=[O:3])[NH:35][C:36]2[CH:37]=[C:38]([CH2:42][C:43]([OH:45])=[O:44])[CH:39]=[CH:40][CH:41]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 571807(3-Aminophenyl)acetic acidHCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Product 1

HCID 59509064HCID 59509064, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Phenyl chloroformate (0.15 g, 99 mmol) was added dropwise to a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.20 g, 0.99 mmol) and DIPEA (0.250 g, 1.98 mmol) in dry dichloromethane (10 ml) at −78° C. and the mixture was allowed to stir overnight at room temperature. Then dichloromethane was evaporated, dry 1,4-dioxane and (3-amino-phenyl)-acetic acid (0.15 g, 0.99 mmol) were added and the mixture was heated overnight at 70° C. The solvent was evaporated and the crude product was extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with water (2×50 ml) and by brine, dried over anhydrous sodium sulfate and concentrated in a vacuum rotavapor. The residue was washed with ether to give (3-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-phenyl)-acetic acid as a coloured solid.

Workup

  1. customThen dichloromethane was evaporated
  2. temperaturethe mixture was heated overnight at 70° C
  3. customThe solvent was evaporated
  4. extractionthe crude product was extracted with ethyl acetate (2×100 ml)
  5. washThe combined organic phases were washed with water (2×50 ml) and by brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in a vacuum rotavapor
  8. washThe residue was washed with ether

Sources & evidence

ORD record
ord-f9c8b1d2f9844e4489d83e2f222d8ac0
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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