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Hydrochloric Acid → 1,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-3-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1722402
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1722402
C[O:2][C:3]1[N:4]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:6]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[C:7]([CH3:9])[N:8]=1.CO.Cl>O1CCCC1>[CH3:9][C:7]1[NH:8][C:3](=[O:2])[N:4]([C:25]([NH:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[CH:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:6]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 148551061,6-Dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Produkt 1

HCID 148017361,2,3,4-Tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-3-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl esterAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1,6-dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester (3.00 g, 6.45 mmol) in tetrahydrofuran (50 ml)/methanol (25 ml) was treated with 1 N hydrochloric acid (6.0 ml, pH 1) and stirred at room temperature for 1 hour. The reaction was quenched with saturated sodium bicarbonate and partially evaporated. The residue was partitioned between chloroform and water. The organic phase was washed with saturated sodium chloride, dried (magnesium sulfate) and evaporated. The residue was crystallized from dichloromethane/isopropyl ether. The solids which precipitated were recrystallized to give the title compound as a colorless electrostatic solid (1.84 g), melting point 184°-185° C. TLC (5% ethyl acetate/dichloromethane) single spot, Rf =0.39.

Aufarbeitung

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. custompartially evaporated
  3. customThe residue was partitioned between chloroform and water
  4. washThe organic phase was washed with saturated sodium chloride
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was crystallized from dichloromethane/isopropyl ether
  8. customThe solids which precipitated
  9. customwere recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-9e4f5aab06cb41e89e2f2709beac330e
Quelldatensatz
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04855301

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