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

HRID 1692988Notes

Reaction equation

HRID 1692988 reaction equation
[OH-].[Na+].[C@@H]1([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[S:14])O[C@H](CO)[C@@H](O)[C@H]1O.CI.[C:22](O)(=O)C>O.C1COCC1>[CH3:22][S:14][C:13]1[NH:15][C:16](=[O:17])[CH:18]=[CH:19][N:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 30364432-Thiouridine

Product 1

HCID 798232-(Methylthio)-1H-pyrimidin-4-oneYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium hydroxide (6.24 g, 156.07 mmol) in H2O (55 mL) at room temperature is added thiouridine (10 g, 78.03 mmol). The resulting mixture is stirred at room temperature for 20 min. Methyl iodide (5.45 mL, 87.40 mmol) in THF (10 mL) is added dropwise slowly and the mixture is stirred at room temperature for 18 hours. A white solid forms upon acidifying the mixture to pH 5 with glacial acetic acid. The mixture is allowed to stand at 0° C. (ice bath) for 2 hours and filtered to afford 7.4 g (67% yield) of the desired compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 2.45 (s, 3H), 6.07 (d, J=6.6 Hz, 1H), 7.85 (d, J=6.6 Hz, 1H).

Workup

  1. stirringthe mixture is stirred at room temperature for 18 hours
  2. customto stand at 0° C.
  3. customfor 2 hours
  4. filtrationfiltered

Sources & evidence

ORD record
ord-bb1b22f0878e402d88896f6d95abd968
Source dataset
uspto-grants-2012_04
Patent number
US08158641B2

Reaction notes

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