Diethyl (ethoxymethylene)malonate → HCID 54315930, compound
Reaction equation
CO[C:3]1[CH2:7][CH2:6][CH2:5][N:4]=1.C(OC(=O)[C:12](=[CH:18]OCC)[C:13]([O:15]CC)=O)C.[C:23]([O-])(=O)[CH3:24].[NH4+:27]>>[CH2:23]([C:18]1[N:27]=[C:3]2[CH2:7][CH2:6][CH2:5][N:4]2[C:13](=[O:15])[CH:12]=1)[CH3:24]Participants
Procedure
The preparation of pyrrolo[1,2-a]pyrimidines has not been studied thoroughly heretofore [Advances in Heterocyclic Chemistry Vol. 21, pp. 3-25 (1977), edited by Academic Press] and only some references have been published concerning the preparation of 3-substituted-pyrrolo[1,2-a]pyrimidines. [Chem. Commun. 805 (1966); Khim. Geterosikl. Soedin, 3, 428, 1970 and 6, 765 1975; C. R. Hebd. Seances Acad. Sci., Ser C. 262, 365, 1966 and 265, 249, 1967; Bull. Soc. Chim. Fr. 9, 3133, 3139 and 3146, 1969, Justus Liebigs Ann. Chem. 103, 1973; Chem. Ber. 103, 1797, 1970 and 107, 270, 1974; Chem. Pharm. Bull. 21, 1305, 1973; and DE-Patent Specification No. 1 803 758 and Japanese Patent Specification No. 7 334 897 and HU-Patent Specification No. 167 676⟧ According to HU-patent Specification No. 167 676, 2-methoxy-1-pyrroline is heated with diethyl-ethoxymethylene-malonate for 8 hours in the presence of ammonium acetate and the reaction mixture is processed in a complicated manner to give ethyl 4oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine with a yield of 7.1%. No melting point of the product is given. The product is characterized only by IR and PMR spectra.
Sources & evidence
- ORD record
- ord-8ce44bf7d53444c982c250bce16c870c
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04482557
Reaction notes
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