HCID 178432679, compound → 2,6-dimethyl-4-oxo-1H-pyrimidine-5-carbonitrile

HRID 1501103Notes

Reaction equation

HRID 1501103 reaction equation
Br[C:2]1[C:3]([OH:10])=[N:4][C:5]([CH3:9])=[N:6][C:7]=1[CH3:8].[C:11]([Zn]C#N)#[N:12]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[OH:10][C:3]1[C:2]([C:11]#[N:12])=[C:7]([CH3:8])[N:6]=[C:5]([CH3:9])[N:4]=1

Participants

5

Reactant 2

HCID 178432679HCID 178432679, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 1784327532,6-dimethyl-4-oxo-1H-pyrimidine-5-carbonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-bromo-2,6-dimethylpyrimidin-4-ol (3.7 g, 18.3 mmol), dicyano zinc (10.7 g, 91.5 mmol) and tetrakis(triphenylphosphine)palladium (6.3 g, 5.1 mmol) and N,N-dimethylformamide (60 mL) was stirred at 140° C. for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give 4-hydroxy-2,6-dimethylpyrimidine-5-carbonitrile as a white solid (2.7 g, 99%). LRMS (M+H) m/z: calcd 149.06. found 149.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-0545ab9ab3d0429f95a24402c54a3bf2
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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