Tetrahydrofuran → 5-Bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

HRID 4673

Reaktionsgleichung

Reaktionsgleichung von HRID 4673
P(Br)(Br)[Br:2].OC1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)=[N:8][CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10](C)C=1C.C(=O)([O-])[O-].[K+].[K+].O1[CH2:39][CH2:38][CH2:37][CH2:36]1>C1C=CC=CC=1>[Br:2][CH2:36][C:37]1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)=[N:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][C:38]=1[CH3:39]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 704198775-Hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Produkt 1

HCID 104300785-Bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of phosphorus tribromide (16.85 g) in a mixture of benzene (150 ml) and tetrahydrofuran (150 ml) was dropwise added a solution of 5-hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g) in tetrahydrofuran (150 ml) under cooling at 7°-10° C. After stirring for 4 hours at the same temperature, the reaction mixture was poured into ice-water (200 ml), adjusted to pH 9.5 with saturated potassium carbonate and extracted with ethyl acetate (300 ml). After filtering off an insolble material, the organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from diethyl ether to give 5-bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (29.08 g).

Aufarbeitung

  1. temperatureunder cooling at 7°-10° C
  2. extractionextracted with ethyl acetate (300 ml)
  3. filtrationAfter filtering off an insolble material
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5445957897b14e47a375be80f7ca2538
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727073

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