Methyl 4-sulfanylbenzoate → 1-(4-Methyloxycarbonylphenylthio)methyl-5-iodopyrimidin-2-one

HRID 1982568Notes

Reaction equation

HRID 1982568 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11]Cl)=[CH:6][CH:5]=1.SC1C=CC(C(OC)=O)=CC=1.[Na].[I:26][C:27]1[CH:28]=[N:29][C:30](=[O:33])[NH:31][CH:32]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][N:31]2[CH:32]=[C:27]([I:26])[CH:28]=[N:29][C:30]2=[O:33])=[CH:6][CH:5]=1)=[O:13]

Participants

6

Reactant 4

HCID 237573Methyl 4-sulfanylbenzoateHCID 5360545SodiumHCID 119590965-Iodopyrimidin-2-olHCID 20161330Methyl4-(chloromethylthio)benzoate2×

Product 1

HCID 201613441-(4-Methyloxycarbonylphenylthio)methyl-5-iodopyrimidin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl4-(chloromethylthio)benzoate [The methyl 4-(chloromethylthio)benzoate reagent was made in the conventional manner as previously described for its analogues in Preparations 1 and 4 by chloromethylation of methyl 4-mercaptobenzoate; yield 92%](8.2 mmol) in DMF (10 ml) was added dropwise to a stirred suspension of the sodium salt of 5-iodopyrimidin-2-one (8.2 mmol) in DMF (50 ml) and the final mixture heated at 60° C. for 3h. The solvent was then distilled off, the residue triturated with water and with a little ether. The product was a mixture of the N- and O-isomers in the ratio 4:1; yield 1.50 g (45%). The title compound, the N-isomer, was obtained after fractional crystallisation from ethyl acetate and methanol, m.p. 210° C. NMR

Workup

  1. distillationThe solvent was then distilled off
  2. customthe residue triturated with water and with a little ether
  3. additiona mixture of the N-

Sources & evidence

ORD record
ord-f5a3c1224ae54ec983ff98e3de986dd5
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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