Sodium hydride → 2-Amino-4-(benzo[1,3]dioxol-5-yl-cyano-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1161751

반응식

HRID 1161751 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:16][C:9]2[N:10]=[C:11]([NH2:15])[N:12]=[C:13](Cl)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][C:27]#[N:28])=[CH:25][C:20]=2[O:19][CH2:18]1.[H-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[S:16][C:9]2[N:10]=[C:11]([NH2:15])[N:12]=[C:13]([CH:26]([C:24]3[CH:23]=[CH:22][C:21]4[O:17][CH2:18][O:19][C:20]=4[CH:25]=3)[C:27]#[N:28])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 781783,4-(Methylenedioxy)phenylacetonitrileHCID 16096301Ethyl 2-amino-4-chlorothieno(2,3-d)pyrimidine-6-carboxylate

생성물 1

HCID 595193392-Amino-4-(benzo[1,3]dioxol-5-yl-cyano-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 2-amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1 equiv.) and benzo[1,3]dioxol-5-yl-acetonitrile (1 mole eq.) in DMF at room temperature, sodium hydride (1.1 mole eq., 60% in mineral oil) was added. The mixture was stirred at this temperature overnight under argon. After that, it was diluted with brine and extracted with ethyl acetate. The combined organic portions were washed with brine and water and dried with sodium sulphate. After filtration and evaporation of the solvent, brown solids were obtained which were purified either by preparative TLC or preparative HPLC.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic portions were washed with brine and water
  3. dry with materialdried with sodium sulphate
  4. filtrationAfter filtration and evaporation of the solvent
  5. custombrown solids were obtained which
  6. customwere purified either by preparative TLC or preparative HPLC

출처 및 근거

ORD 기록
ord-50556edcd4944f3f82b2e4db022dc2f8
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820658B2

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