Sodium ethoxide → HCID 59395636, compound
Reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=O)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].O[NH:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=[NH:29].[O-]CC.[Na+]>CCO>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[O:22][N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[N:27]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 140 °C
Procedure
To a mixture of ethyl 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (120 mg, 0.32 mmol) and of N-hydroxy-2-pyridinecarboximidamide (50 mg, 0.36 mmol) in EtOH (2 ml) was added a 21% (w/v) solution of sodium ethoxide in EtOH (0.225 ml, 0.62 mmol) and then heated in a sealed vial in a microwave oven at 140° C. for 10 min. The cooled mixture was evaporated to dryness and the residue partitioned between chloroform (5 ml) and saturated aqueous ammonium chloride (5 ml). The organic phase was evaporated to dryness and the crude product subjected to purification by MDAP. Product containing fractions were combined and evaporated to dryness. The product was triturated to a solid in a small amount of diethyl ether then dried to reveal the title compound as a white solid (44 mg, 31%).
Workup
- customThe cooled mixture was evaporated to dryness
- customthe residue partitioned between chloroform (5 ml) and saturated aqueous ammonium chloride (5 ml)
- customThe organic phase was evaporated to dryness
- customthe crude product subjected to purification by MDAP
- additionProduct containing fractions
- customevaporated to dryness
- customThe product was triturated to a solid in a small amount of diethyl ether
- customthen dried
Sources & evidence
- ORD record
- ord-a5ce854c27e84d26885e53a2ff360a3c
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143264B2
Reaction notes
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