HRID921324

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：COc1cc(P(C)(C)=O)ccc1Nc1nc(Nc2ccccc2S(=O)(=O)C(C)C)c2ccn(COCC[Si](C)(C)C)c2n1

HCID86668794

未命名化合物

PRODUCTS

生成物

结构：COc1cc(P(C)(C)=O)ccc1Nc1nc(Nc2ccccc2S(=O)(=O)C(C)C)c2cc[nH]c2n1

HCID68166174

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3301

Ethylenediamine

C2H8N2

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

To a solution of compound N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine in THF (1 mL) was added tetrabutylammonium fluoride (TBAF) in THF (1.0 M, 3 mL) and ethylenediamine (0.1 mL). The solution was heated at 60° C. for 24 hrs. About 40% conversion was observed by HPLC monitoring. Volatile components were removed on rotavap and the residue was subjected to prep-HPLC purification. The desired product was determined by NMR to be contaminated with TBAF, which was removed by water wash (4 times). Evaporation of EtOAc gave the pure compound (14 mg). MS/ES+: m/z=514.

WORKUP

后处理

customVolatile components were removed on rotavap
customthe residue was subjected to prep-HPLC purification
customwas removed by water
washwash (4 times)
customEvaporation of EtOAc

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7ff640c87374445388c02ee9b048b583
来源数据集: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09273077B2
来源说明: uspto-grants-2016_03

反应 SMILES

[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[C:15]3[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:16]=3[N:17]=2)=[C:7]([O:42][CH3:43])[CH:6]=1)([CH3:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(N)CN>[CH3:4][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:40])[CH3:41])(=[O:37])=[O:38])[C:15]3[CH:20]=[CH:19][NH:18][C:16]=3[N:17]=2)=[C:7]([O:42][CH3:43])[CH:6]=1)([CH3:1])=[O:3]