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Water → Methyl-phenyl-carbamic Acid 5-(4-methoxy-phenoxy)-pyrimidin-2-yl Ester

HRID 1831252
Notes
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Reaction equation

HRID 1831252 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:9]=[N:10][C:11]([OH:14])=[N:12][CH:13]=2)=[CH:5][CH:4]=1.[CH3:17][N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20].N12CCN(CC1)CC2.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:9]=[N:10][C:11]([O:14][C:19](=[O:20])[N:18]([CH3:17])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:12][CH:13]=2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178492489HCID 178492489, compound

Product 1

HCID 69519671Methyl-phenyl-carbamic Acid 5-(4-methoxy-phenoxy)-pyrimidin-2-yl EsterYield 79%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of 5-(4-methoxy-phenoxy)-pyrimidin-2-ol (0.44 g, 2.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.34 g, 2.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.22 g, 2.00 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 1 hour. Water was added and the precipitates were collected by suction. The solids were dissolved in dichloromethane and the solution was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was crystallised from ethyl acetate:heptane yielding the title compound (0.55 g, 79% yield) as an off-white solid.

Workup

  1. customthe precipitates were collected by suction
  2. dissolutionThe solids were dissolved in dichloromethane
  3. dry with materialthe solution was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-c77f3327d0ec4f45963a5402eeeebf45
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067517B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes