Acetic Acid → 2-(Methylthio)-1H-pyrimidin-4-one

HRID 2172862Notes

Reaction equation

HRID 2172862 reaction equation
[S:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][NH:3]1.CI.[CH3:11]COC(C)=O.CC(O)=O>[OH-].[Na+]>[CH3:11][S:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 1269845Thiouracil

Product 1

HCID 798232-(Methylthio)-1H-pyrimidin-4-oneYield 54%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-thioxo-2,3-dihydropyrimidin-4(1H)-one (66.7 g, 0.497 mol) was dissolved in aq. NaOH (41.6 g of solid in 365 mL of H2O). The mixture was then treated with CH3I (100.1 g, 0.704 mol) and was stirred at room temperature for 18 h. TLC (petroleum ether: EtOAc=4:1) indicated that the reaction was complete. The resulting mixture was adjusted to pH=5˜6 with HOAc (30 mL). The solid formed was collected and dried on vacuum to give title compound (40 g, 54%) as a white solid.

Workup

  1. customThe solid formed
  2. customwas collected
  3. customdried on vacuum

Sources & evidence

ORD record
ord-ca0e2213b8604086ae8d5a6fd7dc3a40
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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