2-(Ethoxymethylene)propanedinitrile → 4-Amino-2-(ethylthio)-5-pyrimidinecarbonitrile

HRID 1059635Notes

Reaction equation

HRID 1059635 reaction equation
C[O-].[Na+].I.[CH2:5]([S:7][C:8](=[NH:10])[NH2:9])[CH3:6].C(O[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])C>CCO>[NH2:19][C:18]1[C:15]([C:16]#[N:17])=[CH:14][N:9]=[C:8]([S:7][CH2:5][CH3:6])[N:10]=1

Participants

5

Reactant 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 10942334Sodium MethoxideHCID 12295709S-ethylisothiourea hydroiodide

Product 1

HCID 95501744-Amino-2-(ethylthio)-5-pyrimidinecarbonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A suspension of NaOMe (2.7 g, 50 mmol) in EtOH (200 mL) is added to a mixture of S-ethylisothiourea hydroiodide (11.58 g, 50 mmol), ethoxymethylidenemalo-nonitrile (6.1 g, 50 mmol) and ethanol (250 mL) at 25° C. The reaction mixture is refluxed under N2 for 2 h, and then the solution is concentrated on a hot plate until precipitation is observed. After cooling, the solid is collected by suction filtration and is stirred in water at 25° C. Filtration and vacuum oven drying affords 4-amino-5-cyano-2-ethylthiopyrimidine (4.02 g, 45%) as a brown solid. 1H NMR δ (DMSO) 8.45 (1H, s), 7.90 (2H, brs), 3.00 (2H, q, J=7.3 Hz), 1.27 (3H, t, J=7.3 Hz).

Workup

  1. temperatureThe reaction mixture is refluxed under N2 for 2 h
  2. concentrationthe solution is concentrated on a hot plate until precipitation
  3. temperatureAfter cooling
  4. filtrationthe solid is collected by suction filtration
  5. filtrationFiltration and vacuum oven
  6. customdrying

Sources & evidence

ORD record
ord-26ad1384fda2497284cab887aedcd930
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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