2-Chloropyrimidine → HCID 3696466, compound

HRID 1043691Notes

Reaction equation

HRID 1043691 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][CH:9]1[O:14][CH:13]([CH3:15])[CH2:12][NH:11][CH2:10]1.C(N(C(C)C)CC)(C)C>C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:11]1[CH2:10][CH:9]([CH3:8])[O:14][CH:13]([CH3:15])[CH2:12]1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 1108622,6-Dimethylmorpholine

Product 1

HCID 3696466HCID 3696466, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL recovery flask, 2-chloropyrimidine (1 g, 8.73 mmol), 2,6-dimethyl morpholine (cis:trans mixture, 1.106 g, 9.60 mmol), N,N-diisopropyl-N-ethylamine (1.241 g, 9.60 mmol), and ethanol (17.46 mL) were added and refluxed for seven hours. Upon completion of the reaction, the solvent was distilled off, and saturated sodium bicarbonate was added thereto. The resulting mixture was extracted with ethyl acetate twice, and the organic phase was washed with saturated brine and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→1:2) to give the title compound (1.29 g, 76%, cis:trans mixture).

Workup

  1. temperaturerefluxed for seven hours
  2. customUpon completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionsaturated sodium bicarbonate was added
  5. extractionThe resulting mixture was extracted with ethyl acetate twice
  6. washthe organic phase was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→1:2)

Sources & evidence

ORD record
ord-f8e24b0123624cd4a721858dbb2c642c
Source dataset
uspto-grants-2013_10
Patent number
US08563552B2

Reaction notes

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