Ethyl Acetoacetate → HCID 117821132, compound

HRID 59127Notes

Reaction equation

HRID 59127 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=O)[CH3:4].[Cl:12][C:13]1[N:18]=C(Cl)C=[C:15]([CH2:20][O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:14]=1.[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1>[Cl:12][C:13]1[N:18]=[C:8]([CH2:7][C:6]([O:5][CH2:3][CH3:4])=[O:11])[CH:10]=[C:15]([CH2:20][O:21][CH2:22][C:23]([F:24])([F:26])[F:25])[N:14]=1

Participants

7

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1178209122,4-Dichloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

Product 1

HCID 117821132HCID 117821132, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) suspension of NaH (400 mg, 9.96 mmol, 60% in oil) in THF (8 mL) was slowly added ethylacetoacetate (1.45 mL, 11.5 mmol). The solution was allowed to stir at rt for 10 min then concentrated in vacuo. The residue was rapidly put under N2. A solution of 2,4-dichloro-6-[(2,2,2-trifluoroethoxy)methyl]pyrimidine (2.0 g, 7.66 mmol) in toluene (38 mL) was added to the residue. The reaction mixture was stirred under reflux for 16 h. Ammonium chloride (aq, 1 mL) was added and stirred vigorously for 10 min. Silica was added and the mixture was concentrated. The residue was purified on a silica gel cartridge eluting with 0% to 40% EtOAc/heptanes to give ethyl the title compound, 600 mg (28%).

Workup

  1. concentrationthen concentrated in vacuo
  2. stirringThe reaction mixture was stirred
  3. temperatureunder reflux for 16 h
  4. stirringstirred vigorously for 10 min
  5. additionSilica was added
  6. concentrationthe mixture was concentrated
  7. customThe residue was purified on a silica gel cartridge
  8. washeluting with 0% to 40% EtOAc/heptanes

Sources & evidence

ORD record
ord-fc010d97ab344e6791e44b3be64f1f28
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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