N,N,N',N'-Tetramethylethylenediamine → 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one

HRID 538224Notes

Reaction equation

HRID 538224 reaction equation
CN(CCN(C)C)C.[NH:9]1[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]1=[O:11].[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>CO.O.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH2:14][C:13]1[CH:15]=[CH:16][N:9]([C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[C:10](=[O:11])[N:12]=1

Participants

7

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2856454-Fluorophenylboronic acidHCID 178418229Cytosine

Product 1

HCID 682901544-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-oneYield 321.7%

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

TMEDA (8 mL, 54 mmol) was added to a stirred suspension of cytosine (3 g, 27 mmol), 4-fluorophenylboronic acid (7.55 g, 5 mmol) and copper(II)acetate monohydrate (5.44 g, 27 mmol) in a mixture of MeOH (960 mL) and H2O (240 mL). The mixture was stirred at RT for 16 hours. The solvents were evaporated in vacuo and the crude product purified by open column chromatography (silica; MeOH in DCM with a gradient of 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with MeOH and DCM and the solid formed filtered and dried in vacuo to yield 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one (3.3 g, 60% yield) as a white solid.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe crude product purified by open column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo
  5. customThe product was triturated with MeOH and DCM
  6. customthe solid formed
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-06c4d9bb11ff4528a1d71d26c51293e7
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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