2-Bromopropiophenone → HCID 12795556, compound

HRID 980175Notes

Reaction equation

HRID 980175 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH:10]([CH3:19])[C:11](=[O:12])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 164522-BromopropiophenoneHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 12795556HCID 12795556, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-chloropyrimidin-2-one (394 mg) and α-bromopropiophenone (0.5 ml) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for 2.75 hours. The solution was evaporated and the residue was triturated with water (50 ml) giving an oily solid. This was extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4) and evaporated to a gum. This was crystallised from acetone-petrol (b.p. 40°-60°) to give the title pyrimidinone (306 mg,); m.p. 125°-127°; λmaxEtOH 232 nm (ε 15400), 245 nm (ε 15480), 335 nm (ε 3970).

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated with water (50 ml)
  3. customgiving an oily solid
  4. extractionThis was extracted with ethyl acetate (3×50 ml)
  5. washThe combined extracts were washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated to a gum
  8. customThis was crystallised from acetone-petrol (b.p. 40°-60°)

Sources & evidence

ORD record
ord-8b8b8a0d58e64cd387ca4abc58f8b5ca
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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