Potassium Carbonate → 1,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1788750Notes

Reaction equation

HRID 1788750 reaction equation
[CH3:1][O:2][C:3]1[NH:4][C:5]([CH3:24])=[C:6]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:31]1([CH2:37][CH2:38][CH2:39]Br)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1OCCOCCOCCOCCOCCOC1>CN(C)C=O.CCOCC>[CH3:1][O:2][C:3]1[N:4]([CH2:39][CH2:38][CH2:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:5]([CH3:24])[C:6]([C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 2855718-Crown-6HCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

Product 1

HCID 572168171,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(3-phenylpropyl)-5-pyrimidinecarboxylic acid, 1-methylethyl esterYield 60.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (4.0 g, 12.0 mmol) in dry dimethylformamide (10 ml) under argon was treated with finely ground potassium carbonate (4.97 g, 36.0 mmoles), 3-phenylpropyl bromide (2.19 ml, 14.4 mmoles) and a catalytic amount of 18-crown-6. The resulting suspension was allowed to stir at room temperature for 72 hours, diluted with ether, filtered and the filtrate washed with water and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated. The residue was purified by flash chromatography (10-15% ethyl acetate in hexanes) to provide the desired product (3.29 g) as a yellow oil.

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with water and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography (10-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-97229f5d221e4003a7da36fedb95fb89
Source dataset
uspto-grants-1987_08
Patent number
US04684655

Reaction notes

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