Methanol → HCID 67454721, compound

HRID 2276783Notes

Reaction equation

HRID 2276783 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[N:10][C:9]([NH2:12])=[N:8][CH:7]=1.CO.[Br:15]Br>O>[Br:15][C:5]1[S:1][C:2]([C:6]2[N:11]=[N:10][C:9]([NH2:12])=[N:8][CH:7]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 674539471,2,4-Triazin-3-amine, 6-(2-thiazolyl)-

Product 1

HCID 67454721HCID 67454721, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a vial was added 6-(thiazol-2-yl)-1,2,4-triazin-3-amine (600 mg, 3.4 mmol), methanol (1.2 mL), water (0.6 mL). The mixture was cooled to 0° C. and bromine (816 mg, 5.1 mmol) was added. The reaction was stirred for 45 min and then quenched with saturated sodium bicarbonate solution (20 mL) and extracted three times with ethyl acetate (50 mL). The organic layers were dried over Na2SO4, concentrated, and purified using silica gel chromatography to afford 320 mg of 6-(5-bromothiazol-2-yl)-1,2,4-triazin-3-amine as an off-white solid.

Workup

  1. customquenched with saturated sodium bicarbonate solution (20 mL)
  2. extractionextracted three times with ethyl acetate (50 mL)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-fcc3d55894514696860e6a69ecb92efb
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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