Sodium hydride → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(2-pyrimidinyloxy)ethoxymethyl]-1,4-dihydropyridine

HRID 2290716Notes

Reaction equation

HRID 2290716 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([CH3:20])[NH:13][C:12]([CH2:21][O:22][CH2:23][CH2:24][OH:25])=[C:11]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].Cl[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([CH3:20])[NH:13][C:12]([CH2:21][O:22][CH2:23][CH2:24][O:25][C:32]2[N:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[C:11]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 703535674-(2-Chlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Product 1

HCID 202108534-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(2-pyrimidinyloxy)ethoxymethyl]-1,4-dihydropyridineYield 12.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)-5-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°.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 days
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution washed successively with 2M hydrochloric acid, 5% aqueous sodium carbonate solution and brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was crystallised from ether

Sources & evidence

ORD record
ord-4f83930e914a4a318f64f9a406c77edc
Source dataset
uspto-grants-1986_10
Patent number
US04618609

Reaction notes

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