Hydrochloric Acid → 5-acetyl-2-(methylthio)pyrimidin-4(3H)-one

HRID 2359772Notes

Reaction equation

HRID 2359772 reaction equation
[C:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[S:10])[NH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].[CH3:14]I.Cl>>[C:1]([C:4]1[C:5](=[O:11])[NH:6][C:7]([S:10][CH3:14])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 14798Sodium HydroxideHCID 127555615-Acetyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 566989835-acetyl-2-(methylthio)pyrimidin-4(3H)-oneYield 69.1%

Conditions

Temperature
40 °C

Procedure

5-Acetyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (Ryan Scientific) (2.3 g, 13.51 mmol) was dissolved in NaOH (20.27 mL, 20.27 mmol), then MeI (0.894 mL, 14.30 mmol) was added to the reaction mixture while stirring. The reaction mixture was heated at 40° C. for 1.5 hours. Additional MeI (0.894 mL, 14.30 mmol) was added and the reaction was allowed to stir at rt for 18 hours. The reaction mixture was cooled with an ice-water bath, acidified to pH 6 with concentrated HCl solution, then the resulting precipitate was filtered to obtain 1.72 g of the desired product (69% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.49 (br. s., 6H) 8.35 (s, 1H) 13.40 (br. s., 1H). MS (ES+): m/z=185.1 (100) [MH+]. HPLC: tR=1.0 minute over 3 minutes. Purity: >90% [HPLC (LC/MS) at 220 nm].

Workup

  1. stirringto stir at rt for 18 hours
  2. temperatureThe reaction mixture was cooled with an ice-water bath
  3. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-9d96ea510c4a47a7b6f7643f25ca6763
Source dataset
uspto-grants-2014_04
Patent number
US08685993B2

Reaction notes

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