Acetonitrile → 2-(7-methylspiro[2H-benzofuran-3,1'-cyclopropane]-4-yl)oxy-5-nitro-pyrimidine

HRID 527622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527622
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]2[C:10]3([CH2:12][CH2:11]3)[CH2:9][O:8][C:7]=12.C(#N)C.Cl[C:18]1[N:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1>>[CH3:1][C:2]1[C:7]2[O:8][CH2:9][C:10]3([CH2:12][CH2:11]3)[C:6]=2[C:5]([O:13][C:18]2[N:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 825442-Chloro-5-nitropyrimidineHCID 574113017-methylspiro[2H-benzofuran-3,1-cyclopropane]-4-ol2×

Produkt 1

HCID 679602182-(7-methylspiro[2H-benzofuran-3,1'-cyclopropane]-4-yl)oxy-5-nitro-pyrimidineAusbeute 86,2 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-ol (Intermediate 156, 176 mg, 1 mmol) in dry Acetonitrile (4 ml) potassium carbonate (207 mg, 1.5 mmol) and then 2-chloro-5-nitropyrimidine (159 mg, 1 mmol) were added and the reaction mixture was stirred for 24 hours at 80° C. After cooling the reaction mixture was quenched with water (2 ml), diluted with brine (10 ml) and extracted with ethyl acetate (2×20 ml). The organic layer was dried over sodium sulfate, filtered and evaporated affording the title compound (258 mg) as an orange solid that was used in the next step as crude material without further purification.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture
  2. customwas quenched with water (2 ml)
  3. additiondiluted with brine (10 ml)
  4. extractionextracted with ethyl acetate (2×20 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-709db8c0162445179a8a3d3fd13fb3c4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346790B2

Notizen zur Reaktion

Wird geladen…