Bromine → (+)-6-(3,4-Difluorophenyl)-1,2,3,6-tetrahydro-2-oxo-5-methoxycarbonyl-4-bromomethyl-1-[(4-nitrophenyloxy)carbonyl]pyrimidine

HRID 1840323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840323
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:14]([C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:16])[C:13]([O:27]C)=[N:12][C:11]([CH3:29])=[C:10]2[C:30]([O:32][CH3:33])=[O:31])[CH:5]=[CH:6][C:7]=1[F:8].[Br:34]Br>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:14]([C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:16])[C:13](=[O:27])[NH:12][C:11]([CH2:29][Br:34])=[C:10]2[C:30]([O:32][CH3:33])=[O:31])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 10671680HCID 10671680, Verbindung

Produkt 1

HCID 22725192(+)-6-(3,4-Difluorophenyl)-1,2,3,6-tetrahydro-2-oxo-5-methoxycarbonyl-4-bromomethyl-1-[(4-nitrophenyloxy)carbonyl]pyrimidineAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a well stirred solution of (+)-6-(3,4-difluorophenyl)-1,6-dihydro-2-methoxy-5-methoxycarbonyl-4-methyl-1-[(4-nitrophenyloxy)carbonyl]pyrimidine (1.5 mmol, 0.66 g) in 5 mL of chloroform was added a solution of bromine (1.5 mmol, 0.09 mL) in 3 mL of chloroform at 0° C. and the solution was allowed to attain room temperature over 1.5 h. The solvent was removed in vacuo and the residue was again dissolved in CHCl3, (20 mL) and washed with brine. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo to get 0.81 g of (+)-6-(3,4-difluorophenyl)-1,6-dihydro-2-oxo-5-methoxycarbonyl-4-bromomethyl-1-[(4-nitrophenyloxy)carbonyl]pyrimidine as a yellow foam. It was used in the next step without any purification. 1H NMR δ3.75 (s, 3 H), 4.67 (ABq, dA=4.56, dB=4.78, J=10.8 Hz, 2 H), 6.35 (s, 1 H), 7.09-7.19 (m, 4 H), 7.37 (d, J=9.0 Hz, 2 H), 8.27 (d, J=9.0 Hz, 2 H).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was again dissolved in CHCl3, (20 mL)
  3. washwashed with brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-37b5fb97d25e4cd68ad97b7cf0def086
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680323B2

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