Sodium Hydroxide → 4-[(6-Amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-3-pyrimidinyl)methyl]benzonitrile

HRID 2050797Notes

Reaction equation

HRID 2050797 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[NH2:11][C:12]1[N:17]([CH3:18])[C:16](=[O:19])[NH:15][C:14](=[O:20])[CH:13]=1.[OH-].[Na+]>C(O)C>[NH2:11][C:12]1[N:17]([CH3:18])[C:16](=[O:19])[N:15]([CH2:10][C:3]2[CH:4]=[CH:5][C:6]([C:8]#[N:9])=[CH:7][CH:2]=2)[C:14](=[O:20])[CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 755206-Amino-1-methyluracilHCID 140048403-Bromo-4-methylbenzonitrile

Product 1

HCID 151364174-[(6-Amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-3-pyrimidinyl)methyl]benzonitrileYield 12.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

α - Bromo - p - tolunitrile (5.41 g, 27.6 mmol) was added at once with stirring to a solution of 6-amino-1-methyluracil (V. Papesch and E.F. Schroeder. J. Org. Chem. (1951), 16, 1879) (3.90 g. 27.6 mmol) in 1:1 ethanol: 1 N sodium hydroxide (56 ml) at 42° C. After 1.75 hours. the mixture was cooled, filtered and washed with water. The resulting solid and second crop obtained by evaporation of the filtrate were combined (5.80 g) and partially purified by silica gel chromatography followed by repeated trituration with 1:2 methanol; ether to give crude 4-[(6-Amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-3-pyrimidinyl)methyl]benzonitrile (0.86 g), indentified by NMR.

Workup

  1. additionwas added at once
  2. customat 42° C
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. washwashed with water
  6. customThe resulting solid and second crop obtained by evaporation of the filtrate
  7. custompartially purified by silica gel chromatography

Sources & evidence

ORD record
ord-f47b0e6d1f9a49afa2fc5bda351f59ca
Source dataset
uspto-grants-1991_05
Patent number
US05015647

Reaction notes

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