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Citric Acid → 3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-6-(methylamino)-2,4(1H,3H)-pyrimidinedione

HRID 2224170
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2224170
C(O)(C)(C)C.C(O)C.[BH4-].[Na+].[CH:11]1([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([N:21]=[CH:22]N(C)C)[N:16]([C:26]3[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=3[F:33])[C:15]2=[O:34])[CH2:13][CH2:12]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH:11]1([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([NH:21][CH3:22])[N:16]([C:26]3[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=3[F:33])[C:15]2=[O:34])[CH2:12][CH2:13]1
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Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 21460813HCID 21460813, VerbindungHCID 67024888(E)-N'-(1-Cyclopropyl-3-(2-fluoro-4-iodophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-N,N-dimethylformimidamide

Produkt 1

HCID 597171713-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-6-(methylamino)-2,4(1H,3H)-pyrimidinedione
Ausbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, to t-butanol-ethanol [2:1 (volume ratio), 250 ml] was added sodium borohydride (6.41 g), and the mixture was stirred at room temperature for 1 hr. Under water-cooling, N′-[1-cyclopropyl-3-(2-fluoro-4-iodo-phenyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine 76 (50.0 g) was added, and the mixture was stirred for 2.5 hrs. Under water-cooling, water (225 ml) and 10% aqueous citric acid solution (175 ml) were successively added dropwise, and the mixture was stirred for 3 hrs. The precipitated crystals were collected by filtration and dried to give crude crystals (34.5 g, LC purity 91%) of 3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-6-methylamino-1H-pyrimidine-2,4-dione 52, which were used for the next reaction without purification.

Aufarbeitung

  1. temperatureUnder water-cooling
  2. stirringthe mixture was stirred for 2.5 hrs
  3. temperatureUnder water-cooling
  4. stirringthe mixture was stirred for 3 hrs
  5. filtrationThe precipitated crystals were collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e3e6cbd5aaf2466799ce10cd5f72eb8a
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07378423B2

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