Formic Acid → 9-(4-Hydroxy-2-(hydroxymethyl)butyl)guanine
Reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:15][CH2:16][OH:17])[CH2:13][OH:14])=[C:4](Cl)[N:3]=1.C(O)=[O:20]>>[OH:17][CH2:16][CH2:15][CH:12]([CH2:13][OH:14])[CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:20])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2Participants
Procedure
A solution of (-)-2-(2-amino-6-chlorpurin-9-ylmethyl)-1,4-butanediol (11.5 mg, 0.0423 mmol) in 50% aqueous formic acid (0.75 ml) was kept at 100° C./2 h and then evaporated to dryness, dissolved in 2 ml of water and lyophilized. The product was dissolved in 1 ml of water, 2 drops of conc. aqueous ammonia was added and the solution kept at 100° C. for 10 min, flushed with nitrogen to remove ammonia, and lyophilized. The residue was dissolved by warming with 1.2 ml of 20% aqueous methanol and the solution filtered and kept in open air to allow for slow partial evaporization of solvent. Crystalline needles were formed. Filtration, washing with 3 drops of water and drying yielded 6.4 mg (60%) of (-)-9-(4-hydroxy-2-hydroxymethylbutyl)guanine.
Workup
- customwas kept at 100° C.
- custom2 h
- customevaporated to dryness
- dissolutiondissolved in 2 ml of water
- dissolutionThe product was dissolved in 1 ml of water
- addition2 drops of conc. aqueous ammonia was added
- customflushed with nitrogen
- customto remove ammonia
- dissolutionThe residue was dissolved
- temperatureby warming with 1.2 ml of 20% aqueous methanol
- filtrationthe solution filtered
- customCrystalline needles were formed
- filtrationFiltration
- washwashing with 3 drops of water
- customdrying
Sources & evidence
- ORD record
- ord-c5c9c43c52cc495480d85b10640eb183
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05565461
Reaction notes
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