Yes, a base such as TEA would be fine usually. Though actually in this particular case, since you have a pyridine, perhaps K2CO3 would be better since you can't acid wash out the TEA, but water will get the carbonate salt. Run it in dry DMF, MeCN, or THF at RT.
PS. I just reread your first post. if you use chloroacetylchloride, little alkylation will occur at the amine, since the amine will react with the acid chloride side to give an amide. During that reaction, it is possible to for williamson ether to occur with the hydroxy and alkyl halide and up with dimers. In my experience Williamson ether is usually a crappy reaction with low yields.
Thank you sir, really appreciate your help As i understand, chloro acetylchloride would react with the amino group with high yield but it would be contaminated with a little amide at N1 of pyimidine or alkylation at OH. But i could obtain pure product by simple crystallization. Am i true? or need column chromatography. Thanks again
Yes, a base such as TEA would be fine usually. Though actually in this particular case, since you have a pyridine, perhaps K2CO3 would be better since you can't acid wash out the TEA, but water will get the carbonate salt. Run it in dry DMF, MeCN, or THF at RT.
PS. I just reread your first post. if you use chloroacetylchloride, little alkylation will occur at the amine, since the amine will react with the acid chloride side to give an amide. During that reaction, it is possible to for williamson ether to occur with the hydroxy and alkyl halide and up with dimers. In my experience Williamson ether is usually a crappy reaction with low yields.
Thank you sir, really appreciate your help As i understand, chloro acetylchloride would react with the amino group with high yield but it would be contaminated with a little amide at N1 of pyimidine or alkylation at OH. But i could obtain pure product by simple crystallization. Am i true? or need column chromatography. Thanks again
Yes, a base such as TEA would be fine usually. Though actually in this particular case, since you have a pyridine, perhaps K2CO3 would be better since you can't acid wash out the TEA, but water will get the carbonate salt. Run it in dry DMF, MeCN, or THF at RT.
PS. I just reread your first post. if you use chloroacetylchloride, little alkylation will occur at the amine, since the amine will react with the acid chloride side to give an amide. During that reaction, it is possible to for williamson ether to occur with the hydroxy and alkyl halide and up with dimers. In my experience Williamson ether is usually a crappy reaction with low yields.
Yes, a base such as TEA would be fine usually. Though actually in this particular case, since you have a pyridine, perhaps K2CO3 would be better since you can't acid wash out the TEA, but water will get the carbonate salt. Run it in dry DMF, MeCN, or THF at RT.
PS. I just reread your first post. if you use chloroacetylchloride, little alkylation will occur at the amine, since the amine will react with the acid chloride side to give an amide. During that reaction, it is possible to for williamson ether to occur with the hydroxy and alkyl halide and up with dimers. In my experience Williamson ether is usually a crappy reaction with low yields.
The N-acetylation is vastly preferred. I would not be surprised if simply mixing them together with a proton scavenger gives nearly pure N-acetylated product in less than an hour.
The N-acetylation is vastly preferred. I would not be surprised if simply mixing them together with a proton scavenger gives nearly pure N-acetylated product in less than an hour.
The N-acetylation is vastly preferred. I would not be surprised if simply mixing them together with a proton scavenger gives nearly pure N-acetylated product in less than an hour.
Could you please specify the reaction condition? Did you mean to use a base as TEA or what??
The N-acetylation is vastly preferred. I would not be surprised if simply mixing them together with a proton scavenger gives nearly pure N-acetylated product in less than an hour.
Could you please specify the reaction condition? Did you mean to use a base as TEA or what??
As i understand, chloro acetylchloride would react with the amino group with high yield but it would be contaminated with a little amide at N1 of pyimidine or alkylation at OH. But i could obtain pure product by simple crystallization. Am i true? or need column chromatography.
Thanks again
As i understand, chloro acetylchloride would react with the amino group with high yield but it would be contaminated with a little amide at N1 of pyimidine or alkylation at OH. But i could obtain pure product by simple crystallization. Am i true? or need column chromatography.
Thanks again
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PS. I just reread your first post. if you use chloroacetylchloride, little alkylation will occur at the amine, since the amine will react with the acid chloride side to give an amide. During that reaction, it is possible to for williamson ether to occur with the hydroxy and alkyl halide and up with dimers. In my experience Williamson ether is usually a crappy reaction with low yields.
PS. I just reread your first post. if you use chloroacetylchloride, little alkylation will occur at the amine, since the amine will react with the acid chloride side to give an amide. During that reaction, it is possible to for williamson ether to occur with the hydroxy and alkyl halide and up with dimers. In my experience Williamson ether is usually a crappy reaction with low yields.
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I would expect to see 90+% this if you added those two compounds together in the presence of a proton scavenger.
I would expect to see 90+% this if you added those two compounds together in the presence of a proton scavenger.
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Did you mean to use a base as TEA or what??
Did you mean to use a base as TEA or what??
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