Water → 3-{2-Amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-benzyloxypyridine

HRID 1862276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862276
O.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[O:16][C:17]1[CH:22]=[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])[C:20]([F:36])=[CH:19][C:18]=1[N+:37]([O-])=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:37][C:18]1[CH:19]=[C:20]([F:36])[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:31])([F:33])[F:32])[N:25]([CH3:34])[C:24]2=[O:35])=[CH:22][C:17]=1[O:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 2

HCID 962Water2×HCID 186192594-Benzyloxy-3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}pyridine

Produkt 1

HCID 186191803-{2-Amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-benzyloxypyridineAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a mixture of 0.55 g of an iron powder, 3 ml of acetic acid and 0.3 ml of water was added a solution of 0.548 g of 4-benzyloxy-3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}pyridine in 0.5 ml of acetic acid and 3 ml of ethyl acetate dropwise. After completion of the addition, the mixture was stirred for 3 hour at 40-50° C. The mixture was poured into water, then, the mixture was filtrated through Celite, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, and saturated saline, dried over anhydrous magnesium sulfate, and concentrated to obtain 0.438 g of 3-{2-amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-benzyloxypyridine.

Aufarbeitung

  1. additionAfter completion of the addition
  2. filtrationthe mixture was filtrated through Celite
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-49e8535922d0428ca2081cbf877c53e0
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06537948B1

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