Diethyl Malonate → 4-((4,6-Dihydroxypyrimidin-2-yl)amino)benzonitrile

HRID 1908949Notes

Reaction equation

HRID 1908949 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5]CC)=O.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH2:23])=[NH:22])=[CH:16][CH:15]=1)#[N:13].[Na]>C(O)C>[OH:9][C:1]1[CH:2]=[C:3]([OH:5])[N:23]=[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[N:22]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 178510065HCID 178510065, compound

Product 1

HCID 1785100404-((4,6-Dihydroxypyrimidin-2-yl)amino)benzonitrileYield 93.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (30 gm) was added to 1-(4-cyanophenyl)guanidine (30 gm) at room temperature. A solution of sodium (17.2 gm) in ethanol (450 ml) was added to the above reaction mass. The contents were heated to reflux and maintained for 12 hours. Distilled off the solvent completely under vacuum and then added water (500 ml). The reaction mass was stirred for 30 minutes and filtered. The solid obtained was dried to obtain 40 gm of 4-(4,6-dihydroxypyrimidine-2-yl-amino)benzonitrile.

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux
  3. temperaturemaintained for 12 hours
  4. distillationDistilled off the solvent completely under vacuum
  5. filtrationfiltered
  6. customThe solid obtained
  7. customwas dried

Sources & evidence

ORD record
ord-db95016f3c0e4cf9bc49e189d4ebbc5c
Source dataset
uspto-grants-2013_12
Patent number
US08598341B2

Reaction notes

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