5-Chloro-2(1H)-pyrimidinone → 5-Chloro-1-[1-(2-thenoyl)ethyl]pyrimidin-2-one

HRID 1906155Notes

Reaction equation

HRID 1906155 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH:10]([CH3:18])[C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=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]([C:11](=[O:12])[C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH3:18])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 117699522-Bromo-1-(thiophen-2-yl)propan-1-one

Product 1

HCID 127912555-Chloro-1-[1-(2-thenoyl)ethyl]pyrimidin-2-oneYield 29.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (522 mg) and 2-(2-bromopropionyl)thiophene (965 mg) in triethylamine (0.84 ml) and ethanol (25 ml) was stirred at room temperature. After 3 h. the mixture was heated to 50° C. After a further 1 h. the solvent was removed and the residue dissolved in ethyl acetate (50 ml) which was washed with water (3×25 ml) and brine, dried (MgSO4) and evaporated to a yellow oil. The oil was triturated with diethyl ether and the resulting solid was crystallised twice from ethyl acetate to give the title pyrimidinone (320 mg), m.p. 128°-129° C., λmax (EtOH) 226 nm (ε 11,340), 263 nm (ε10,050), 290 nm (ε 8,950).

Workup

  1. temperatureAfter 3 h. the mixture was heated to 50° C
  2. customAfter a further 1 h. the solvent was removed
  3. dissolutionthe residue dissolved in ethyl acetate (50 ml) which
  4. washwas washed with water (3×25 ml) and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a yellow oil
  7. customThe oil was triturated with diethyl ether
  8. customthe resulting solid was crystallised twice from ethyl acetate

Sources & evidence

ORD record
ord-ce476ec554bd49b9b28a8498abbf4ca2
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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