2-Chloroethanol → 2-[(4-Pyrimidinylmethyl)thio]ethanol

Participants

Reaction Steps

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).

Provenance & Evidence