Acetone → 1-(Pyrimidin-2-yl)propan-2-one

HRID 633911Notes

Reaction equation

HRID 633911 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].CC(N=NC(C#N)(C)C)(C#N)C.Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.Cl>C1COCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[CH2:1][C:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6547AzobisisobutyronitrileHCID 744042-Chloropyrimidine

Product 1

HCID 126566631-(Pyrimidin-2-yl)propan-2-oneYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL flask, acetone (1.44 mL, 19.6 mmol) was added to KH (30% in oil, 2.89 g, 21.6 mmol) in THF (15 mL) at 0° C. under nitrogen. The reaction mixture was stirred for 0.25 h then additional THF (15 mL) was added. AIBN (74 mg, 0.45 mmol) followed by 2-chloropyrimidine (500 mg, 4.36 mmol) were added cautiously and the reaction mixture kept at 0° C. for 1 h. HCl 3N was added until the pH=6. The two layers were separated and the aqueous phase extracted with dichloromethane. The combined extracts were dried over Na2SO4 then concentrated. The residue was purified on column chromatography (eluent: EtOAc/pentane 20/80 to 80/20) to give the title compound (247 mg, 42%) as a yellow oil (keto/enol form 2:1).

Workup

  1. additionwere added cautiously
  2. waitthe reaction mixture kept at 0° C. for 1 h
  3. customThe two layers were separated
  4. extractionthe aqueous phase extracted with dichloromethane
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationthen concentrated
  7. customThe residue was purified on column chromatography (eluent: EtOAc/pentane 20/80 to 80/20)

Sources & evidence

ORD record
ord-a5d07b1914844fd3818f570c78cb4141
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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