SYNTHESIS OF 4-METHYL-6-PHENYL-THIENO[2,3 -D]PYRIMIDINES WITH A FORMAMIDINO OR AN OXALAMIDO CARBONIC-ACID RESIDUE AND ANTIANAPHYLACTIC ACTIVITY

methyl-6-phenyl-thieno[2,3-d]pyrimidine-2-carbonic acid alkylesters 1a , b were hydrolyzed to the potassium salt of the carbonic acid 2. Cycl ization of 2 with acetanhydride yielded the tricyclic 1,3-oxazinone de rivative 4. This compound reacted with pyrrolidine by different condit ions of reaction to give the bisamide 7, the acetamidino carbonic acid 5 and their decarboxylated product 6. Compound 1 a yielded with Vilsm eier reagens the formamidino compound 3. 3-Amino-thieno[2,3-d]pyrimidi n-2-carbonitrile gave under different conditions of reaction with oxal ic acid diethylester or with oxalic acid ethylester chloride the tetra cyclic henyl-thieno[2,3-d:4,5-d']di-pyrimidine-2-carbonic acid methyle ster 10 or the thyl-6-phenyl-thieno[2,3-d]pyrimid-3-yl)oxalamidic ethy lester 12. These compounds were hydrolyzed to give the carbonic acids 11 and 13. Some of the synthesized substances showed an anti-anaphylac tic activity.