HRID240611

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6101

4-Methylbenzenesulfonic acid

C7H8O3S

HCID516892

Sodium Bicarbonate

CHNaO3

HCID2759834

Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

C9H7ClN2O2S

结构：CC(C)(C)OC(=O)N1CCC[C@H](Oc2cc(F)ccc2N)C1

HCID58413089

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1sc2ncnc(Nc3ccc(F)cc3O[C@H]3CCCN(C(=O)OC(C)(C)C)C3)c2c1C

HCID58413026

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 70 °C

PROCEDURE

实验过程

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (1.17 g), (S)-tert-butyl 3-(2-amino-5-fluorophenoxy)piperidine-1-carboxylate (Intermediate 1.1 g) was dissolved in dioxane (10 ml) and p-toluenesulfonic acid (61 mg) was added. The reaction was heated at 70° C. for 1.5 h. The solution was poured into sat. NaHCO3 (50 ml) and extracted with chloroform. The organic phases were passed through a phase separator and concentrated in vaco. The sample was purified by chromatography (silica gel; solvent: isohexan:EtOAc 3:1→2:1) to give the desired product.

WORKUP

后处理

extractionextracted with chloroform
concentrationconcentrated in vaco
customThe sample was purified by chromatography (silica gel; solvent: isohexan:EtOAc 3:1→2:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7ad2fbc504214d30bb261400b1bdc7c8
来源数据集: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08648068B2
来源说明: uspto-grants-2014_02

反应 SMILES

[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][C:17]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:18]=1[O:19][C@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:16][C:17]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:18]=3[O:19][C@H:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)[C:7]=2[C:6]=1[CH3:15])=[O:4]