Malononitrile → 4-Amino-5-pyrimidinecarbonitrile

HRID 2285591Notes

Reaction equation

HRID 2285591 reaction equation
[C:1](O)(=O)C.[CH:5]([NH2:7])=[NH:6].[C:8](#[N:12])[CH2:9][C:10]#[N:11].[O-]CC.[Na+].[Na]>C(O)C>[NH2:6][C:5]1[C:9]([C:8]#[N:12])=[CH:10][N:11]=[CH:1][N:7]=1

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 160693Formamidine acetateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 7372084-Amino-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Formamidine acetate (104.11 g., 1.00 mole) and malononitrile (33.03 g., 0.50 mole) are added to a solution of sodium ethoxide prepared from sodium (24.2 g., 1.05 mole) and absolute ethanol (750 ml.) in a nitrogen atmosphere. The mixture is stirred at room temperature for 48 hours. The off-white solid which separates is collected by filtration, washed with ice water then dried at 80° C./house vac. (ca. 200 mm.). The yield of product melting at greater than 340° C. (uncorr.) is 28.5 g. (47.0%). Recrystallization of this material from water (Darco G-60) affords cream-colored needles melting at 250° C. dec. (uncorr.) in a yield of 11.3 g. (18.8%).

Workup

  1. filtrationThe off-white solid which separates is collected by filtration
  2. washwashed with ice water
  3. customthen dried at 80° C./house vac
  4. customRecrystallization of this material from water (Darco G-60)

Sources & evidence

ORD record
ord-ec7ca274854345bab0acd3dab70295c9
Source dataset
uspto-grants-1982_04
Patent number
US04323681

Reaction notes

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