Ethanol → HCID 12791249, compound

HRID 1906154Notes

Reaction equation

HRID 1906154 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[S:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:12].C(O)C>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11](=[O:12])[C:13]2[S:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 122897372-Bromo-1-(5-methyl-2-thienyl)ethanone

Product 1

HCID 12791249HCID 12791249, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (522 mg) and 2-bromoacetyl-5-methylthiophene (1.30) g) in triethylamine (0.84 ml) and ethanol (25 ml) was stirred at room temperature. After 2 h. the mixture was concentrated to ca. 10 ml, diluted with ethyl acetate (100 ml), washed with water (×3) and brine, dried (MgSO4) and evaporated to a gum. The gum was triturated with diethyl ether and the resulting solid dissolved in ethanol and treated with charcoal. Evaporation of the solvent followed by recrystallisation of the residue twice from ethyl acetate gave the title pyrimidinone (205 mg) m.p. 199°-203° C., εmax (EtOH) 226.5 nm (ε8,570), 261.5 nm (ε9,280), 297 nm (ε11,630).

Workup

  1. concentrationAfter 2 h. the mixture was concentrated to ca. 10 ml
  2. additiondiluted with ethyl acetate (100 ml)
  3. washwashed with water (×3) and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a gum
  6. customThe gum was triturated with diethyl ether
  7. dissolutionthe resulting solid dissolved in ethanol
  8. additiontreated with charcoal
  9. customEvaporation of the solvent
  10. customfollowed by recrystallisation of the residue twice from ethyl acetate

Sources & evidence

ORD record
ord-f05a06ceedf54610a75304f1a941df22
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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