1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amine

HRID 2069142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069142
[NH2:1][C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C1CCN2C(=NCCC2)CC1.F[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([N+:31]([O-:33])=[O:32])=[CH:23][CH:22]=1>CS(C)=O.CO.C(O)(C(F)(F)F)=O>[N+:31]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[CH:3]=2)=[CH:22][CH:23]=1)([O-:33])=[O:32]

Komponenten

7

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2617641-Fluoro-4-nitronaphthaleneHCID 1354312726-Amino-1H-pyrimidin-4-one

Produkt 1

HCID 585325356-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amineAusbeute 16,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 887MethanolLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a solution of 6-aminopyrimidin-4(3H)-one (866 mg, 7.79 mmol) in DMSO (10.0 mL) at RT was added DBU (1.29 mL, 8.57 mmol) and after 30 min a solution of 1-fluoro-4-nitronaphthalene (1.57 g, 8.18 mmol) in DMSO (3.0 mL) was added over 2 min. The resulting mixture was maintained at RT for 2 hr and was diluted with MeOH (20 mL) and TFA (2.0 mL) was added. The solution was subjected to SCX capture and release and the crude product so obtained was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 50-100%, gradient elution) to afford the title compound as a yellow solid (370 mg, 16.48%); Rt 3.82 min (Method 1 basic); m/z 283 (M+H)+ (ES+)

Aufarbeitung

  1. additionwas added
  2. customthe crude product so obtained
  3. customwas purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 50-100%, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-6bc6d103793d42b18b7c550772a9744a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299074B2

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