Potassium Carbonate → 1,6-Dihydro-2-methoxy-6-methyl-1-[3-[methyl(phenylmethyl)amino]propyl]-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1788753Notes

Reaction equation

HRID 1788753 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+].[CH2:31]([N:38]([CH2:40][CH2:41][CH2:42]Cl)[CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1OCCOCCOCCOCCOCCOC1>CN(C)C=O.CCOCC>[CH3:1][O:2][C:3]1[N:4]([CH2:42][CH2:41][CH2:40][N:38]([CH3:39])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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 22067N-benzyl-3-chloro-N-methylpropan-1-amineHCID 2855718-Crown-6HCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

Product 1

HCID 570770761,6-Dihydro-2-methoxy-6-methyl-1-[3-[methyl(phenylmethyl)amino]propyl]-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl esterYield 50.9%

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-methyethyl ester (2.0 g, 6.0 mmol) in dimethylformamide (7.0 ml) was treated with finely ground potassium carbonate (1.7 g, 12.0 mmoles), N-benzyl-3-chloro-N-methylpropylamine (2.37 g, 12.0 mmol) and a catalytic amount of 18-crown-6. The reaction was heated at 70°-75° C. under argon overnight. The reaction was allowed to cool down to room temperature and was diluted with ether. It was filtered, and the filtrate was washed with water, brine and was dried over anhydrous magnesium sulfate. Evaporation of solvent provided a brown oil which was purified by flash chromatography (20% acetone in hexanes) to yield the title compound (1.51 g) as a yellow oil.

Workup

  1. temperatureThe reaction was heated at 70°-75° C. under argon overnight
  2. filtrationIt was filtered
  3. washthe filtrate was washed with water, brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customEvaporation of solvent
  6. customprovided a brown oil which
  7. customwas purified by flash chromatography (20% acetone in hexanes)

Sources & evidence

ORD record
ord-580a557c2ed64af0a505c01de0c132cc
Source dataset
uspto-grants-1987_08
Patent number
US04684655

Reaction notes

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