Cyanide → HCID 136302346, compound
Reaction equation
[C-:1]#[N:2].[CH3:3][C:4]1[CH2:13][NH:12][C:11]2[N:10]=[C:9]([NH2:14])[NH:8][C:7](=[O:15])[C:6]=2[N:5]=1>>[C:1]([C:4]1([CH3:3])[CH2:13][NH:12][C:11]2[N:10]=[C:9]([NH2:14])[NH:8][C:7](=[O:15])[C:6]=2[NH:5]1)#[N:2]Participants
3
Procedure
The first synthesis of 6,6-disubstituted tetrahydropteridines utilized nucleophilic addition of cyanide across the 7,8 double bond of 6-methyl-7,8-dihydropterin, yielding 6-cyano-6-methyltetrahydropterin (Viscontini et al., Helv. Chim. Acta, 54, 811-818 (1971)). After a number of intermediate steps, the nitrile was reduced and the final compound, 6-aminomethyl-6-methyl-5,6,7,8-tetrahydropterin, was obtained. This molecule proved to be less stable than expected, since upon oxidation the resulting quinoid dihydropterin was able to reform the starting 6-methyl-7,8-dihydropterin by loss of the amino methyl group as ammonia and formaldehyde.
Sources & evidence
- ORD record
- ord-f717473dedfd40c99d3ff9e96d0f455a
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401844
Reaction notes
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