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Water → Morpholine-4-carboxylic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester

HRID 1179870
Notes
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Reaction equation

HRID 1179870 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([OH:9])[N:4]=1.[N:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.N12CCN(CC1)CC2.O>CN(C)C=O.[Cl-].[Na+].O>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:18]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:19])[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 848104-Morpholinecarbonyl chlorideHCID 178517744HCID 178517744, compound

Product 1

HCID 69519825Morpholine-4-carboxylic Acid 4-trifluoromethyl-pyrimidin-2-yl EsterYield 80%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-trifluoromethyl-2-hydroxypyrimidine (0.49 g, 3.00 mmol), 4-morpholinecarbonyl chloride (0.45 g, 3.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.34 g, 3.00 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 1 hour. Water and brine were added and the solution was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70→50:50)) yielding the title compound (0.66 g, 80% yield) as a white solid.

Workup

  1. extractionthe solution was extracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70→50:50))

Sources & evidence

ORD record
ord-a639b64c5605482a8a115cbb8b611c2a
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07279470B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes