HuagongsheHuagongshe Chemistry Print Report · For research reference only
Malonate Ion → 2-(Bis-phenylcarbamoyl-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Malonate Ion | HCID 9084 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Malonanilide | HCID 69298 | — |
| Reactant | 2-Methanesulfonyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester | HCID 59376449 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | tetrahydrofuran N,N-dimethylformamide | HCID 21974620 | — |
| Product | 2-(Bis-phenylcarbamoyl-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester | HCID 59376467 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158825B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-e5912f0c6de84e41b1fbb525d3dcb8b0 |
| Source note | uspto-grants-2012_04 |