Pyridine → HCID 86245271, compound

HRID 2263063Notes

Reaction equation

HRID 2263063 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([NH2:10])=[CH:8][N:7]=[CH:6][N:5]=1)[CH3:2].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19]>O1CCCC1>[CH2:1]([O:3][C:4]1[C:9]([NH:10][C:18](=[O:19])[O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[CH:8][N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 45080306HCID 45080306, compound

Product 1

HCID 86245271HCID 86245271, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-ethoxypyrimidine-5-amine (1.00 g, 7.19 mmol) and pyridine (1.74 ml, 21.6 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.49 ml, 10.8 mmol) with ice-cooling, the mixture was stirred for 30 minutes with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (1.73 g, 76.5%) as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4f2e0b18df454f7f968ae8d397da2ca0
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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