HRID552767

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC

HCID81998

Ethynyltributylstannane

C14H30Sn

结构：CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO[Si](C)(C)C(C)(C)C)O[C@H]2n1cnc2c(Cl)ncnc21

HCID15101786

未命名化合物

PRODUCTS

生成物

结构：C=Cc1ncnc2c1ncn2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]2OC(C)(C)O[C@H]21

HCID67164220

未命名化合物

收率 67.2%

AUXILIARIES

试剂、催化剂与溶剂

结构：Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1

催化剂HCID178418476

未命名化合物

溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

PROCEDURE

实验过程

To a solution of 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloro-9H-purine (330 mg, 0.74 mmol) and tributyl(vinyl)stannane (0.26 mL, 0.88 mmol) in 1,2 dichloroethane (10 mL) was added Pd(Ph3P)2Cl2 (26 mg, 0.03 mmol) and the r×n mixture was heated at reflux overnight. The solvent was removed and the residue purified by flash chromatography (0 to 20% EtOAc/hexanes) to yield 215 mg (67%) of the title compound.

WORKUP

后处理

temperaturethe r×n mixture was heated
temperatureat reflux overnight
customThe solvent was removed
customthe residue purified by flash chromatography (0 to 20% EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9c14bbe1d7db4ba7a9383b9080c3a23f
来源数据集: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07951810B2
来源说明: uspto-grants-2011_05

反应 SMILES

[Si:1]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3Cl)[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC>ClCCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[CH:30]=[CH2:31])[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]