2-Mercapto-3-butanol → 4-(3-Hydroxy-2-butylthiomethyl)pyrimidine
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7]Br)=[N:3][CH:2]=1.[SH:9][CH:10]([CH3:14])[CH:11]([OH:13])[CH3:12]>>[OH:13][CH:11]([CH3:12])[CH:10]([S:9][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][N:3]=1)[CH3:14]Participants
Procedure
By the same method, 4-pyrimidylmethyl bromide is reacted with 3-mercapto-2-butanol to yield 4-(3-hydroxy-2-butylthiomethyl)pyrimidine, with 3-mercapto-1,2-propanediol to yield 4-(2,3-dihydroxy-1-propylthiomethyl)pyrimidine, with 2-mercaptophenol to yield 4-(2-hydroxyphenylthiomethyl)pyrimidine, with ethyl 2-mercaptoacetate to yield ethyl 2-(4-pyrimidylmethylthio)acetate, with ethyl 2-mercaptopropionate to yield ethyl 2-(4-pyrimidylmethylthio)propionate, with ethyl 2-phenyl-2-mercaptoacetate to yield ethyl 2-phenyl-2-(4-pyrimidylmethylthio)acetate (when ethyl esters are prepared, it is preferable to substitute an equivalent of sodium ethoxide for sodium methoxide), with mercaptoacetone to yield 4-pyrimidylmethylthioacetone, with 1-phenyl-1-mercaptoacetone to yield 1-(4-pyrimidylmethylthio)-1-phenylacetone, and with methyl 3-mercaptopropionate to yield methyl 3-(4-pyrimidylmethylthio)propionate (when methyl esters are prepared it is preferable to substitute methanol for ethanol).
Sources & evidence
- ORD record
- ord-09553125c8c54a55adf7ca1f56e826e1
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04246263
Reaction notes
Loading…