HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(2-pyrimidinyloxy)ethoxymethyl]-1,4-dihydropyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloropyrimidine | HCID 74404 | — |
| Reactant | 4-(2-Chlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-3-methoxycarbonyl-6-methyl-1,4-dihydropyridine | HCID 20210848 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(2-pyrimidinyloxy)ethoxymethyl]-1,4-dihydropyridine | HCID 20210853 | 25.3% |
Reaction Steps
Sodium hydride (90 mg. of an 80% by weight dispersion in oil) was added to a solution of 4-(2-chlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-3-methoxycarbonyl-6-methyl-1,4-dihydropyridine (0.60 g) in tetrahydrofuran (20 ml) and the mixture stirred at room temperature for 45 minutes and then treated with 2-chloropyrimidine (0.17 g). The mixture was stirred at room temperature for 3 days and evaporated. The residue was dissolved in ethyl acetate and the solution washed successively with 2M hydrochloric acid, 5% aqueous sodium carbonate solution and brine, dried over MgSO4 and evaporated. The residue was crystallised from ether to give the title compound (90 mg), m.p. 101°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04654353 |
| Source dataset | uspto-grants-1987_03 |
| ORD ID | ord-7f2f798299164eeb8108792d544163e5 |
| Source note | uspto-grants-1987_03 |