Potassium Carbonate → HCID 20491779, compound

HRID 434661Notes

Reaction equation

HRID 434661 reaction equation
[Cl:1][C:2]1[C:3]([S:10][CH3:11])=[N:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].Cl[CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([S:10][CH3:11])=[N:4][C:5](=[O:9])[N:6]([CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698302-(Chloromethyl)thiopheneHCID 204917685-Chloro-6-methyl-4-(methylsulfanyl)pyrimidin-2(1H)-one

Product 1

HCID 20491779HCID 20491779, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-chloro-6-methyl-4-methylthiopyrimidin-2-one (1.768 g), 2-chloromethylthiophene (1.505 g) and potassium carbonate (2.499 g) in dry N,N-dimethylformamide (20 ml) was stirred and heated at ca 90° C. for 30 min. The reaction mixture was evaporated to dryness and the residue was partitioned between ethyl acetate (200 ml) and water (50 ml). The organic phase was washed with brine (50 ml), dried (MgSO4) and evaporated to a brown solid. Preparative layer chromatography on silica developing with chloroform-ethanol (20:1, two runs) gave a solid which was crystallised from acetone to give cream crystals of the title pyrimidinone (362 mg) m.p. 173°-176° C.; λmax (EtOH) 231.5 nm (ε 17030), 276 nm (ε 9360), 320 nm (ε 10010).

Workup

  1. temperatureheated at ca 90° C. for 30 min
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue was partitioned between ethyl acetate (200 ml) and water (50 ml)
  4. washThe organic phase was washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to a brown solid
  7. customPreparative layer chromatography on silica developing with chloroform-ethanol (20:1, two runs) gave a solid which
  8. customwas crystallised from acetone

Sources & evidence

ORD record
ord-a34e01e325c040f3a33baa43b70d0642
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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