Hydrogen Bromide → HCID 11564642, compound

HRID 895108Notes

Reaction equation

HRID 895108 reaction equation
CO[CH:3](OC)[CH2:4]Br.Br.C(=O)([O-])O.[Na+].[NH2:14][C:15]1[C:16](=[O:24])[N:17]([CH3:23])[C:18]([S:21][CH3:22])=[N:19][N:20]=1>CC(O)C.CO.O>[CH3:23][N:17]1[C:16](=[O:24])[C:15]2=[N:14][CH:3]=[CH:4][N:20]2[N:19]=[C:18]1[S:21][CH3:22]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 516892Sodium BicarbonateHCID 115428516-Amino-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 11564642HCID 11564642, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Bromoacetaldehyde dimethyl acetal (2.57 g, 13.1 mmol), 48% hydrobromic acid (1.06 g, 13.1 mmol) and water (1.5 ml) were heated at 95° C. for 1.5 h. The mixture was allowed to cool to ambient temperature, diluted with propan-2-ol (20 ml) then treated with sodium hydrogen-carbonate (1.46 g, 17.4 mmol) added in portions over 5 min. The mixture was filtered and the filtrate was added to 6-amino-4-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one (1.50 g, 8.71 mmol). The resulting suspension was heated at 95° C. for 18 h. The mixture was allowed to cool to ambient temperature, diluted with methanol (100 ml) and evaporated onto silica. The product was purified by flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (3-6%). Collecting appropriate fractions gave 3-methyl-2-methylsulfanyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one (0.81 g, 47%) as a pale yellow solid: δH (400 MHz, CDCl3) 2.61 (3H, s), 3.58 (3H, s), 7.49 (1H, d, J1), 7.52 (1H, d, J1).

Workup

  1. additionadded in portions over 5 min
  2. filtrationThe mixture was filtered
  3. temperatureThe resulting suspension was heated at 95° C. for 18 h
  4. temperatureto cool to ambient temperature
  5. customevaporated onto silica
  6. customThe product was purified by flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (3-6%)
  7. customCollecting appropriate fractions

Sources & evidence

ORD record
ord-e08e8b942b9947eebdad846b05b4f39a
Source dataset
uspto-grants-2005_07
Patent number
US06914060B2

Reaction notes

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