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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: karl26 on September 13, 2007, 06:12:45 AM

Title: 2-amino pyrimidine + phenyl chloroformate
Post by: karl26 on September 13, 2007, 06:12:45 AM

HI ,


Does anyone know if a 2-amino pyrimidine will react with a chloroformate ( methy, phenyl...) under Schoten-Baumann conditions (DCM/NaOH aq, RT, strong stirring)


many thanks for your help  ;)

Title: Re: 2-amino pyrimidine + phenyl chloroformate
Post by: lavoisier on September 13, 2007, 01:12:51 PM

I guess it will react.
However, I'm not sure how stable the carbamate that you form will be.
Methyl and partly phenyl carbamates are a bit sensitive to basic hydrolysis, and your amine is not a 'standard' one.
But if you work at low temperature and quickly, you might get away with it.

Title: Re: 2-amino pyrimidine + phenyl chloroformate
Post by: AWK on September 14, 2007, 07:42:34 AM

Chloroformates are very reactive reagents. At Schotten-Baumann conditions they probably decompose in some extent. At least 5-fold excess will be needed.

Title: Re: 2-amino pyrimidine + phenyl chloroformate
Post by: karl26 on September 14, 2007, 08:35:18 AM

thanks for your answer. do you expect chloroformate to be more reactive than acyl chloride (RCOCl)  ? because Schoten-Baumann reaction using acid chloride are done with 1.5 eq. of acyl chloride.


thanks  ;)