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

HRID 1097661Notes

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][C:19]([O:21]CC)=O)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4].[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([CH2:35]/[C:36](=[N:39]/[H])/[NH:37]O)[CH:31]=[CH:32][C:33]=1[OH:34])[CH3:26].[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][C:19]2[O:21][N:39]=[C:36]([CH2:35][C:30]3[CH:31]=[CH:32][C:33]([OH:34])=[C:28]([O:27][CH2:25][CH3:26])[CH:29]=3)[N:37]=2)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

Ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate (53 mg, 0.15 mmol) and (1Z)-2-[3-(ethyloxy)-4-hydroxyphenyl]-N-hydroxyethanimidamide (35 mg, 0.165 mmol; entry 11, Table 7) were mixed in EtOH (0.75 ml). Ethanolic sodium ethoxide (21% by wt., 0.083 ml, 0.22 mmol) was added and the mixture was heated in the microwave at 140° C. for 10 min. A further 0.055 ml (0.15 mmol) of NaOEt solution was then added and the mixture heated for a further 10 min period at 140° C. The mixture was partitioned between EtOAc and 2M HCl and the organic phase evaporated and purified by MDAP to give the title compound as a solid (29.6 mg).

Workup

temperaturethe mixture heated for a further 10 min period at 140° C
customThe mixture was partitioned between EtOAc and 2M HCl
customthe organic phase evaporated
custompurified by MDAP

Sources & evidence

ORD record: ord-abc9f693b5fd4726a272b4e4fb058db2
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143264B2

Reaction notes

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