Sodium ethoxide → 3-Butyl-8-chloro-1-{4-[3-(3-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097705Notes

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]=[C:32]([OH:36])[CH:31]=1)=[NH:29].CC[O-].[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]=[C:32]([OH:36])[CH:31]=3)[N:27]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of ethyl 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (50 mg, 0.13 mmol), N,3-dihydroxybenzenecarboximidamide (25 mg, 0.16 mmol), 21% solution of NaOEt in EtOH (55 μl, 0.15 mmol) and EtOH (1.5 ml) was heated in the microwave at 180° C. for 10 min. Another aliquot of 21% solution of NaOEt in EtOH (55 μl, 0.21 mmol) was added and the mixture heated in the microwave at 175° C. for 30 min. After cooling the reaction was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, concentrated and purified by the MDAP. The title compound was obtained as an off-white solid (20 mg, 32%).

Workup

temperaturethe mixture heated in the microwave at 175° C. for 30 min
temperatureAfter cooling the reaction
customwas partitioned between 2M HCl (aq) and EtOAc
customThe organic layer was separated
concentrationconcentrated
custompurified by the MDAP

Sources & evidence

ORD record: ord-6ff108dc657746cf8c807dd9086a6003
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143264B2

Reaction notes

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