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 1788753노트

반응식

HRID 1788753 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-580a557c2ed64af0a505c01de0c132cc
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04684655

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