Benzyl Bromide → 3-Benzyl-5-chloro-2-methyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

HRID 1795974Notes

Reaction equation

HRID 1795974 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:11]=[CH:12][N:13]2[C:18]=1[C:17](=[O:19])[NH:16][C:15]([CH3:20])=[N:14]2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[CH2:1]([N:16]1[C:17](=[O:19])[C:18]2=[C:10]([Cl:9])[CH:11]=[CH:12][N:13]2[N:14]=[C:15]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 1357525045-chloro-2-methyl-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Product 1

HCID 221800473-Benzyl-5-chloro-2-methyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-oneYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

Benzyl bromide (9.97 ml, 83.9 mmol) was added to a solution of 5-chloro-2-methyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (14 g, 76.3 mmol) and Cs2CO3 (29.7 g, 91.5 mmol) in dioxane (300 mL). The reaction mixture was stirred at 95° C. for 3 h, cooled to room temperature, filtered through Celite® and the filtrate concentrated in vacuo. The residue was dissolved in CHCl3 (100 mL), treated with saturated NaCl solution (200 mL), and extracted with CHCl3 (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with Et2O, the solid filtered, washed with petroleum ether and dried in vacuo to afford the title compound (19.5 g, 94%) as a white solid: 1H NMR (DMF-d7) δ 7.57 (m, 1H), 7.32–7.41 (m, 5H), 6.65 (m, 1H), 5.31 (s, 2H), 2.38 (s, 3H); MS (ESI+) 274 (M++H), HRMS (ESI+): calculated: 274.0747 (M++H). found: 274.0757 (M++H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThe residue was dissolved in CHCl3 (100 mL)
  5. additiontreated with saturated NaCl solution (200 mL)
  6. extractionextracted with CHCl3 (3×100 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with Et2O
  11. filtrationthe solid filtered
  12. washwashed with petroleum ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-fe70bf7504e44b88bffbb25d13c4c26b
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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