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

Reaction equation

HRID 1161751 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-50556edcd4944f3f82b2e4db022dc2f8
Source dataset
uspto-grants-2010_10
Patent number
US07820658B2

Linked notes

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