Ammonia → 5,6-Diphenylfuro[2,3-d]pyrimidin-4-amine

HRID 502646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502646
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:23].[CH3:24][OH:25]>>[CH3:24][O:25][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:11]1([C:10]2[C:3]3[C:2]([NH2:23])=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 222Ammonia2×HCID 887Methanol2×HCID 114496374-Chloro-5,6-diphenylfuro[2,3-d]pyrimidine

Produkt 2

HCID 2902085,6-Diphenylfuro[2,3-d]pyrimidin-4-amineHCID 115149734-Methoxy-5,6-diphenylfuro[2,3-d]pyrimidine

Versuchsvorschrift

56.9 mg (0.185 mmol) of 4-chloro-5,6-diphenylfuro[2,3-d]pyrimidine 51 and 0.930 mL (1.85 mmol) of 2.0 M ammonia in methanol were combined in a disposable sealed tube and stirred at RT for 15 minutes. The reaction was then heated at 70° C. for 1.5 h. At this point, an additional 0.930 mL (1.85 mmol) of 2.0 M ammonia in methanol was added and the resulting mixture was heated at 70° C. for 3 days, cooled to RT and concentrated. Flash chromatography (SiO2, gradient eluent: 2:1 hexanes-ethylacetate, 2:1 ethyl acetate-hexanes, 9:1 CH2Cl2-MeOH), afforded the title compound 4-methoxy-5,6-diphenylfuro[2,3-d]pyrimidine 53 and 5,6-diphenylfuro[2,3-d]pyrimidin-4-amine 52. Mass found: 303.0 (M+H+); Calculated for C19H14N2O2: 302.

Aufarbeitung

  1. temperatureThe reaction was then heated at 70° C. for 1.5 h
  2. temperaturethe resulting mixture was heated at 70° C. for 3 days
  3. temperaturecooled to RT
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bc483806e6d9442d8cc60e91126ec195
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776867B2

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