HRID1984107

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID784

Hydrogen peroxide

H2O2

HCID516892

Sodium Bicarbonate

CHNaO3

HCID853005

Di-tert-butyl N,N-dipropan-2-ylphosphoramidoite

C14H32NO2P

结构：COc1c(C)cnc(Cn2cc(C#CCCO)c3c(Cl)nc(N)nc32)c1C

HCID11950510

未命名化合物

HCID178418441

未命名化合物

PRODUCTS

生成物

结构：COc1c(C)cnc(Cn2cc(C#CCCOP(=O)(OC(C)(C)C)OC(C)(C)C)c3c(Cl)nc(N)nc32)c1C

HCID57713854

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

A solution of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (4.0 g) and 1-H-tetrazole (0.45 M in acetonitrile, 70 mL) in THF (160 mL) was treated with di-tert-butyl diisopropylphosphoramidite (16.4 mL) at rt for 2 h. The solution was cooled to 0° C. and treated with 30% aqueous H2O2 (11 mL) for 30 mm. Work-up (EtOAc, aq. NaHCO3) and reverse-phase preparative HPLC gave the title compound, as a solid. HPLC Rt=6.13 mm.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-72e59f9aa1b4464f8e4132c7dda8c14e
来源数据集: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07544672B2
来源说明: uspto-grants-2009_06

反应 SMILES

[NH2:1][C:2]1[N:3]=[C:4]([Cl:27])[C:5]2[C:10]([C:11]#[C:12][CH2:13][CH2:14][OH:15])=[CH:9][N:8]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:6]=2[N:7]=1.N1C=NN=N1.C(N(C(C)C)[P:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])(C)C.OO.C([O-])(O)=[O:54].[Na+]>C1COCC1.CCOC(C)=O>[P:37]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])([O:15][CH2:14][CH2:13][C:12]#[C:11][C:10]1[C:5]2[C:4]([Cl:27])=[N:3][C:2]([NH2:1])=[N:7][C:6]=2[N:8]([CH2:16][C:17]2[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=2)[CH:9]=1)=[O:54]