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

HRID 2051172Notes

Reaction equation

HRID 2051172 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[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]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=2)[C:14](=[O:20])[CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 755206-Amino-1-methyluracilHCID 869964-(Bromomethyl)benzonitrile

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

Sources & evidence

ORD record
ord-b08a461e1f794e33b59b208c8bedd138
Source dataset
uspto-grants-1991_05
Patent number
US05017577

Reaction notes

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