2-Chloroethanol → 2-[(4-Pyrimidinylmethyl)thio]ethanol
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][SH:8])=[N:3][CH:2]=1.Cl[CH2:10][CH2:11][OH:12].BrCCO>>[OH:12][CH2:11][CH2:10][S:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][N:3]=1Participants
Procedure
According to the methodology of Examples 11 to 15, 4-pyrimidylmethyl mercaptan is reacted with 2-chloroethanol or 2-bromoethanol to yield 4-(2-hydroxyethylthiomethyl)pyrimidine, with chloroacetone to yield 4-pyrimidylmethylthioacetone, with alphabromoacetophenone to yield alpha-(4-pyrimidylmethylthio)acetophenone, with alpha-bromo-p-methoxyacetophenone to yield alpha-(4-pyrimidylmethylthio)-p-methoxyacetophenone, with alpha-bromo-p-nitroacetophenone to yield alpha-(4-pyrimidylmethylthio)-p-nitroacetophenone, with alpha-bromopropiophenone to yield alpha-(4-pyrimidylmethylthio)propiophenone, with ethyl 2-bromoacetate to yield 2-(4-pyrimidylmethylthio)acetate, with ethyl 2-chloropropionate to yield 2-(4-pyrimidylmethylthio)propionate and with ethyl 2-phenyl-2-bromoacetate to yield 2-phenyl-2-(4-pyrimidylmethylthio)acetate (when ethyl esters are prepared, it is preferable to substitute an equivalent of sodium ethoxide for sodium methoxide; when the corresponding methyl esters are prepared, it is preferable to substitute methanol for ethanol).
Sources & evidence
- ORD record
- ord-b3beba4c86134a509cec1ba0f500a21f
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04246263
Reaction notes
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