Methyl iodide → 2-Methylthio-5-[1-(3-pyridyl)ethyl]-4-pyrimidone

HRID 1905908Notes

Reaction equation

HRID 1905908 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[S:15])[NH:13][CH:14]=2)[CH3:8])[CH:2]=1.[O-][CH2:18]C.[Na+].CI>C(O)C>[CH3:18][S:15][C:12]1[NH:11][C:10](=[O:16])[C:9]([CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH3:8])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 13505307HCID 13505307, compound

Product 1

HCID 135053092-Methylthio-5-[1-(3-pyridyl)ethyl]-4-pyrimidoneYield 113%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-[1-(3-Pyridyl)ethyl]-2-thiouracil (3.4 g) was added to a solution of sodium ethoxide (from 0.74 g sodium) in ethanol (35 ml). Methyl iodide (2.42 g) was added over 0.5 hour at 0°. After standing for a further 2 hours at 0° the solution was evaporated to dryness. The residue was taken up in water and the pH adjusted to 7.0 and the mixture was allowed to stand at 0° overnight. The solid was filtered off to give 2-methylthio-5-[1-(3-pyridyl)ethyl]-4-pyrimidone (3.04 g) m.p. 201°-204° (from ethanol).

Workup

  1. customthe solution was evaporated to dryness
  2. waitto stand at 0° overnight
  3. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-bae385e621bf4f9a83e28ff8c68e3f46
Source dataset
uspto-grants-1987_03
Patent number
US04649141

Reaction notes

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