N-bromobutanimide → HCID 178433466, compound
Reaction equation
[C:1]([C:3]1[C:4]([OH:11])=[N:5][C:6]([CH3:10])=[CH:7][C:8]=1[CH3:9])#[N:2].[Br:12]N1C(=O)CCC1=O>>[Br:12][C:7]1[C:8]([CH3:9])=[C:3]([C:1]#[N:2])[C:4]([OH:11])=[N:5][C:6]=1[CH3:10]Participants
3
Procedure
In a method to prepare 5,6,7-tri-substituted-5-deazapteridines, for example, 3-cyano-2-hydroxy-4,6-dimethylpyridine (commercially available) may be brominated with N-bromosuccinimide, affording the corresponding 5-bromo-3-cyano-2-hydroxy-4,6-dimethylpyridine. The bromo compound was in turn may be treated with phosphorus oxychloride in the presence of N,N -dimethylformamide, yielding 2-chloro-5-bromo-3-cyano-4,6-dimethylpyridine. The so-prepared pyridine was cyclized with quanidine carbonate in N,N-dimethylacetamide, yielding the targeted 5,6,7-trisubstituted-5-deazapteridines, for example, 2,4-diamino-6-bromo-5,7-dimethylformamide. Example 19 provides a detailed description of how this reaction is conducted.
Sources & evidence
- ORD record
- ord-aa9dd86386584df6a0039344056a83f1
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05532370
Reaction notes
Loading…