Methyl 4-sulfanylbenzoate → 1-(4-Methyloxycarbonylphenylthio)methyl-5-iodopyrimidin-2-one
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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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 1.50g (45%). The title compound, the N-isomer, was obtained after fractional crystallisation from ethyl acetate and methanol, m.p. 210° C. NMR (TFA); δ 4.09 (Me), 5.60 (CH2), 7.4-8.2 (Ph), 8.67 (H-4, J4,6 3Hz) 8.87 (H-6). 1R (KBr): 1640 (CO), 1710 cm-1 (CO-ester). MS [70 eV, m/z (% rel. int.)].
Workup
- distillationThe solvent was then distilled off
- customthe residue triturated with water and with a little ether
- additiona mixture of the N-
Sources & evidence
- ORD record
- ord-77a37f8b98fe429daedd3a3e09f4dfbb
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04705791
Reaction notes
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