2-Chloro-5-nitropyrimidine → 2-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-nitropyrimidine

HRID 527551

Reaktionsgleichung

Reaktionsgleichung von HRID 527551
[CH3:1][C:2]1([CH3:12])[C:6]2=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=[C:5]2[O:4][CH2:3]1.Cl[C:14]1[N:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1>CN(C)C=O>[CH3:1][C:2]1([CH3:12])[C:6]2[C:7]([O:11][C:14]3[N:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 825442-Chloro-5-nitropyrimidineHCID 574112993,3-Dimethyl-2,3-dihydro-1-benzofuran-4-ol2×

Produkt 1

HCID 679586942-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-nitropyrimidineAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3,3-dimethyl-2,3-dihydro-1-benzofuran-4-ol (Intermediate 50, 724 mg) in dry N,N-Dimethylformamide (40 mL) potassium carbonate and 2-chloro-5-nitropyrimidine (774 mg, 4.85 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with water (40 ml) and extracted with ethyl acetate (3×40 ml). The combined organic layers were washed with brine (2×50 ml), separated, dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using a column SNAP 50 g and cyclohexane/ethyl acetate as eluents from 100/0 to 70/30 to afford the title compound (1.257 g) as a yellow oil.

Aufarbeitung

  1. customThe reaction was quenched with water (40 ml)
  2. extractionextracted with ethyl acetate (3×40 ml)
  3. washThe combined organic layers were washed with brine (2×50 ml)
  4. customseparated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel using a column SNAP 50 g and cyclohexane/ethyl acetate as eluents from 100/0 to 70/30

Quellen und Nachweise

ORD-Eintrag
ord-91d41efbafce4aa18e70f89123c515be
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346790B2

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