Acetic Acid → 5,6-dimethyl-2-(methylsulfanyl)pyrimidin-4(1h)-one

HRID 63120

Reaction equation

HRID 63120 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=[S:9])[NH:6][C:7]=1[CH3:8].[OH-].[Na+].CI.[C:15](O)(=O)C>O>[CH3:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([S:9][CH3:15])=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 27362495,6-Dimethyl-2-thiouracil

Product 1

HCID 1354949705,6-dimethyl-2-(methylsulfanyl)pyrimidin-4(1h)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5,6-dimethyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (10.0 g, 64.0 mmol, Example 1, Step A) and sodium hydroxide (10.0 g, 260.0 mmol) in water (150 mL) at ambient temperature was added methyl iodide (15.0 g, 320.0 mmol), and the reaction mixture was stirred at ambient temperature overnight. Then the reaction mixture was acidified with acetic acid (50 mL), and the solid was collected by filtration and dried to afford 7.0 g (64%) of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.87 (s, 3H), 2.18 (s, 3H), 2.45 (s, 3H), 12.38 (bs, 1H).

Workup

  1. filtrationthe solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-8b9970a145f54e7f8cdb43222681458b
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Linked notes

Loading…