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Treatment of amide 1b with thiocyanatobenzene provided the corresponding quinazoline in <15% yield under various reaction conditions.
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Treatment of amide 1a with cyanic bromide did give the corresponding 4-bromopyrimidine albeit in low yields (37-56%).
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38
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70350721307
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note
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We have considered mechanisms other than direct nucleophilic addition of 2e to an electrophilic intermediate; however, in the absence of any contrary data, a plausible mechanism based on our prior studies is used here.
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The use of trimethylsilyl cyanide led to decomposition of the activated amide.
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Cyanamide, bis(trimethylsilyl)carbodiimide, and potassium cyanate do not serve as competent nucleophiles under our condensative pyrimidine synthesis reaction conditions; for example, amide 1c and cyanamide did not afford 6u.
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A variety of 2-thiopyrimidine derivatives were synthesized in low yield (<20%) primarily due to the incomplete activation of the carbamothioates.
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