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

HRID 1831237Notes

Reaction equation

HRID 1831237 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>[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

Participants

6

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 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(trifluoromethyl)-2-pyrimidol (0.49 g, 3.00 mmol), 4-morpholinecarbonyl chloride (0.45 g, 3.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.51 g, 3.00 mmol) in N,N-dimethylformamide (15 ml) was stirred at room temperature for 2 hours. Water was 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-488fed786c9d48ad95ce24b4ccd6fb95
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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