HRID230278

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID23394

3-(Chloromethyl)pyridine hydrochloride

C6H7Cl2N

结构：CCOC(=O)C1=C(C)N(c2cccc(C(F)(F)F)c2)C(=S)NC1c1ccc(C#N)cc1

HCID57762441

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)C1=C(C)N(c2cccc(C(F)(F)F)c2)C(SCc2cccnc2)=NC1c1ccc(C#N)cc1

HCID57762456

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID67553

Tetrabutylammonium Iodide

C16H36IN

溶剂HCID180

Acetone

C3H6O

PROCEDURE

实验过程

Ethyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (Example 3; 100 mg, 0.22 mmol), 3-(chloro-methyl)pyridine hydrochloride (40.5 mg, 0.25 mmol), N,N,N-tributyl-1-butan-aminium iodide (7 mg, 0.03 mmol) and potassium carbonate (65.2 mg, 0.47 mmol) are dissolved in 3 ml acetone and stirred at room temperature overnight. The solvent is removed in vacuo and the product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10).

WORKUP

后处理

customThe solvent is removed in vacuo
customthe product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f965d75181da4fd299dee4559eac7cbf
来源数据集: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07566723B2
来源说明: uspto-grants-2009_07

反应 SMILES

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11](=[S:31])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.Cl[CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11]([S:31][CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)=[N:10]2)=[CH:7][CH:8]=1)#[N:2]