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

HRID 1097671Notes

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].Cl.O[NH:27]/[C:28](=[N:37]\[H])/[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[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:37]=[C:28]([CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:27]=2)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

To ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate (26 mg, 0.073 mmol) and (1Z)—N-hydroxy-2-(phenyloxy)ethanimidamide hydrochloride (16 mg, 0.079 mmol) in EtOH (1 ml) was added 21% wt. ethanolic sodium ethoxide solution (0.068 ml, 0.183 mmol) and the mixture was heated under microwave irradiation at 140° C. for 10 min. The mixture was partitioned between EtOAc and 2M HCl, the organic phase dried (Na2SO4) evaporated and purified by MDAP to give title compound as a gum which solidified upon trituration with ether (5.9 mg).

Workup

customThe mixture was partitioned between EtOAc and 2M HCl
dry with materialthe organic phase dried (Na2SO4)
customevaporated
custompurified by MDAP

Sources & evidence

ORD record: ord-6c3354e88e3940f98eda0edd7806d783
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143264B2

Reaction notes

Loading…