Phosphorus oxychloride → 4-Chloro-5-(propan-2-yl)pyrrolo[2,1-f][1,2,4]triazine

HRID 347508Notes

Reaction equation

HRID 347508 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][N:7]2[C:12]=1[C:11](=O)[NH:10][CH:9]=[N:8]2)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:11]1[C:12]2=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=[CH:6][N:7]2[N:8]=[CH:9][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136186059HCID 136186059, compound

Product 1

HCID 210816774-Chloro-5-(propan-2-yl)pyrrolo[2,1-f][1,2,4]triazine

Procedure

5-Isopropylpyrrolo[2,1-f][1,2,4]triazin-4 (3H)-one (0.035 g, 0.198 mmol, 1.0 equiv) was added to phosphorous oxychloride (2.0 ml, 21.5 mmol, 109 equiv) under a nitrogen atmosphere. The reaction mixture was heated to reflux for 1.5 h. The mixture was cooled to room temperature then concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted twice with ethyl acetate. The combined organic washes were dried over anhydrous magnesium sulfate and concentrated in vacuo to yield a tan solid that was used in the next step without further purification. MS(ESI+) m/z 196 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 h
  3. concentrationthen concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. extractionThe aqueous layer was extracted twice with ethyl acetate
  6. dry with materialThe combined organic washes were dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield a tan solid that
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-1c1e2577682b41a0b7ed5b964207cebf
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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