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

HRID 1097670노트

반응식

HRID 1097670 반응식
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15]C(OCC)=O)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1.[OH:27][NH:28]/[C:29](=[N:38]\[H])/[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1.[O-]CC.[Na+]>CCO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]3[O:27][N:28]=[C:29]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=4)[N:38]=3)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 66812467Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoateHCID 178506465N'-hydroxy-2-(4-hydroxyphenyl)ethanimidamide

생성물 1

HCID 593957908-Chloro-1-(3-{3-[(4-hydroxyphenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione수율 17.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (29 mg, 0.078 mmol) and (1Z)—N-hydroxy-2-(4-hydroxyphenyl)ethanimidamide (14 mg, 0.084 mmol) were heated in EtOH (1 ml) with 21% ethanolic sodium ethoxide (0.043 ml, 0.117 mmol) under microwave irradiation at 140° C. for 10 min. The mixture was partitioned between EtOAc and 2M HCl and the organic phase evaporated. This material was stirred with EtOH (1 ml) and 2M NaOH (0.5 ml) for 18 h, before being worked up again by partition between EtOAc and 2M HCl. Purification by MDAP afforded the title compound (6.5 mg).

후처리

  1. customThe mixture was partitioned between EtOAc and 2M HCl
  2. customthe organic phase evaporated
  3. customby partition between EtOAc and 2M HCl
  4. customPurification by MDAP

출처 및 근거

ORD 기록
ord-bc191e1f4aa443b5931a004c1a990bd2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143264B2

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