Ammonia methanol → N,N-Dimethylguanidine
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[CH2:8][NH:9][CH2:10][C:4]=2[C:3]=1[C:11]#[N:12].[NH3:13].[CH3:14]O>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[CH2:8][NH:9][CH2:10][C:4]=2[C:3]=1[C:11]#[N:12].[CH3:14][N:7]([CH3:6])[C:2]([NH2:13])=[NH:1]Participants
Procedure
Two 6,7-dihydropyrrolo[3,4-c]pyrido[2,3-d]pyrimidines which contain a novel tricyclic ring system of potential bilogical interest were sythesized. 6-(2,5-Dimethoxphenyl)-6,7-dihydropyrrolo[3,4-c]pyrido[2,3-d]pyrido[2,3-d]pyridmidine-2,4(1H,3H)-dione (3a) [throughout the Experimental Detail section, numbers in parenthesis () refer to numbered compounds in FIGS. 1 to 4] was prepared from a pyrido[2,3-d]pyrimidine. 6-Acetoxymethyl-5-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4) was oxidized with SeO3 to the corresponding 5-formyl derivative (5) which was condensed with 2,5-dimethoxyaniline to form the Schiff base. Reduction of the exocyclic azomethine double bond of the Schiff base with NaBH3CN to (6) followed by thermal cyclization afforded (3a). 2,4-Diamino-6-(4-methoxyphenyl)-6,7-dihydropyrrolo[3,4-c]pyrido[2,3-d]pyrimidine (3b) was synthesized by addition of a pyrimidine ring to the dihydropyrrolo[3,4-c]pyridine system. 1-(4-Methoxphenyl)pyrrolidine- 3-one (18) was condensed with malononitrile to give a Knoevenagel adduct (19). Treatment of (19) with N,N-dimethylaminomethylene chloride in the presence of LDA afforded the 4-N,N-dimethylaminomethylenepyrrolidine derivative (20) which was converted into 6-amino-7-cyano-2,3-dihydropyrrolo[3,4-c]pyridine (21) by treatment with NH3 /MeOH. Cyclization of (21) with N,N-dimethyl-guanidine afforded the desired product (3b) in high yield.
Sources & evidence
- ORD record
- ord-b63bcba566ca4575aa6682b4e2b36f5c
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04925939
Reaction notes
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