Hydroxyamine hydrochloride → 3-butyl-1-methyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile
Reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH:14]=O)[N:10]([CH2:16][CH:17]=[CH2:18])[C:9]=2[C:8](=[O:19])[N:7]([CH3:20])[C:6]1=[O:21])[CH2:2][CH2:3][CH3:4].Cl.[NH2:23]O>N1C=CC=CC=1>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([C:14]#[N:23])[N:10]([CH2:16][CH:17]=[CH2:18])[C:9]=2[C:8](=[O:19])[N:7]([CH3:20])[C:6]1=[O:21])[CH2:2][CH2:3][CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 3-butyl-1-methyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde in anhydrous pyridine (5 ml) was treated with hydroxylamine hydrochloride (63 mg, 0.91 mmol) and heated at 50° C. for 1 hour. The mixture was allowed to cool, concentrated, and treated with acetic anhydride (5 ml) then heated at 100° C. for 2.5 hours and 125° C. for 45 minutes. Again the mixture was allowed to cool then partitioned between water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated to afford the title compound as a yellow residue (230 mg crude, 114%); m/z 288.3[MH+].
Workup
- temperatureto cool
- concentrationconcentrated
- additiontreated with acetic anhydride (5 ml)
- temperaturethen heated at 100° C. for 2.5 hours and 125° C. for 45 minutes
- temperatureto cool
- customthen partitioned between water and EtOAc
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fe109db5dcfd4f0a8f154682440a3ef8
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394808B2
Reaction notes
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