HRID1945663

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCc1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(C=C3CN(C(=O)OC(C)(C)C)C3)n(C)c2n1

HCID59605202

未命名化合物

PRODUCTS

生成物

HCID59605656

未命名化合物

收率 83.4%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23938

Palladium

溶剂HCID176

Acetic Acid

C2H4O2

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

To a solution of 3-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester (1.1 g, 2.07 mmol) in EtOH (40 mL) and AcOH (15 mL) was added 10% Pd/C (200 mg) and the resulting mixture stirred under an atmosphere of H2 for 65 h. The reaction mixture was filtered through Celite®, washing with EtOAc, and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 70-100%) affording the title compound as an orange oil (0.92 g, 83%). LCMS (method H): RT 3.01 min [M+H]+ 533.4

WORKUP

后处理

filtrationThe reaction mixture was filtered through Celite®
washwashing with EtOAc
concentrationthe filtrate concentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 70-100%)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c8bf6213acd04d0c8c7a2f4d9903d27a
来源数据集: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08394796B2
来源说明: uspto-grants-2013_03

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[CH:12][C:13]2[N:14]([CH3:39])[C:15]3[C:20]([N:21]=2)=[C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:18]=[C:17]([N:28]2[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[N:30]=[C:29]2[CH2:37][CH3:38])[N:16]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.CC(O)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:13]2[N:14]([CH3:39])[C:15]3[C:20]([N:21]=2)=[C:19]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[N:18]=[C:17]([N:28]2[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[N:30]=[C:29]2[CH2:37][CH3:38])[N:16]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]