Malonate Ion → 2-(Bis-phenylcarbamoyl-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 1694851Notes

Reaction equation

HRID 1694851 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[O:9])=[CH:3][CH:2]=1.[H-].[Na+].C([O-])(=O)CC([O-])=O.[CH3:29][O:30][C:31]([C:33]1[S:45][C:36]2[N:37]=[C:38](S(C)(=O)=O)[N:39]=[CH:40][C:35]=2[CH:34]=1)=[O:32]>C1COCC1.C1COCC1.CN(C=O)C>[CH3:29][O:30][C:31]([C:33]1[S:45][C:36]2[N:37]=[C:38]([CH:10]([C:11](=[O:12])[NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8](=[O:9])[NH:7][C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)[N:39]=[CH:40][C:35]=2[CH:34]=1)=[O:32]

Participants

7

Reactant 4

HCID 9084Malonate IonHCID 24758Sodium hydrideHCID 69298Propanediamide, N,N'-diphenyl-HCID 593764492-Methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Product 1

HCID 593764672-(Bis-phenylcarbamoyl-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of malondianilide (102 mg, 0.40 mmol) in THF (2 mL) was added of NaH (16.3 mg, 60% wt. dispersion in mineral oil, 0.41 mmol). After 10 min, the malonate salt solution was added to a solution of 2-methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (100 mg, 0.367 mmol) in THF/DMF (2/0.5 mL). After 1 h, the reaction was quenched with sat. NH4Cl and extracted with EtOAc. The organic layer was washed with brine (1×), dried over MgSO4, filtered, and concentrated. The residue was triturated with EtOAc and H2O, and the solid was filtered.: ESIMS calcd 447 (W+H), found 447 M++H).

Workup

  1. waitAfter 1 h
  2. customthe reaction was quenched with sat. NH4Cl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with EtOAc and H2O
  9. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-e5912f0c6de84e41b1fbb525d3dcb8b0
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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