Hydrogen Bromide → 2-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1356083Notes

Reaction equation

HRID 1356083 reaction equation
[Na].[C:2]([C:4]([C:11]#[N:12])=[C:5]([NH:8][C:9]#[N:10])[S:6][CH3:7])#[N:3].[BrH:13]>C(O)(=O)C>[NH2:10][C:9]1[N:3]=[C:2]([Br:13])[C:4]([C:11]#[N:12])=[C:5]([S:6][CH3:7])[N:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86583755HCID 86583755, compound

Product 1

HCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred suspension of 1.00 g (5.37 mmol) 2,2-dicyano-1-methylsulfanyl-vinyl-cyanamide sodium salt in 10 ml acetic acid at 5° C. was added dropwise 10 ml hydrobromic acid solution (33% in acetic acid) and the mixture was stirred at room temperature for 30 minutes. The mixture was then poured onto 100 ml ice-water added. The resulting crystals were collected by filtration and washed with water (ca 500 ml) until the washings were free of bromide ion. Chromatography (ethyl acetate/hexane 1/4) afforded 1.09 g (83%) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile as a white crystalline solid. EI-MS m/e (%): 246 (M{81Br}+, 93), 244 (M{79Br}+, 94), 165 ([M—Br]+, 100).

Workup

  1. additionadded
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water (ca 500 ml) until the washings

Sources & evidence

ORD record
ord-ce474b633ae6477ca8fc3c09177e2c67
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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