Phosphorus oxychloride → 4-Chloro-5-methylpyrrolo(2,1-f)(1,2,4)triazine

HRID 1072069Notes

Reaction equation

HRID 1072069 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=O)[NH:8][CH:7]=[N:6]2.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:9]1[C:10]2=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357420715-Methylpyrrolo[2,1-f][1,2,4]triazin-4(1H)-one

Product 1

HCID 218742274-Chloro-5-methylpyrrolo(2,1-f)(1,2,4)triazineYield 82%

Conditions

Temperature
100 °C

Procedure

A suspension of of 5-methyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (2.57 gm, 17.2 mmole) in POCl3 (28 mL) was heated at 100° C. for 40 min. The excess reagent was removed under vacuum and the residue was dissolved in DCM (300 mL). This was washed with water, dried (Na2SO4), and the solvent removed. Flash chromatography on silica gel using DCM as eluent afforded the product as a yellow solid (2.38 gm, 82%). 1HNMR (CDCl3): δ 2.63 (s, 3H), 6.74 (d, 1H, J=2 Hz), 7.74 (d, 1H, J=2 Hz), 8.05 (s, 1H).

Workup

  1. customThe excess reagent was removed under vacuum
  2. dissolutionthe residue was dissolved in DCM (300 mL)
  3. washThis was washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-94866feb816140268f00fd6f31f85ceb
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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