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

HRID 2069142Notes

Reaction equation

HRID 2069142 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 585325356-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amineYield 16.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

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+)

Workup

  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)

Sources & evidence

ORD record
ord-6bc6d103793d42b18b7c550772a9744a
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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