Diisopropylethylamine → 4,5-Dichloropyrrolo[2,1-f][1,2,4]triazine

HRID 347518

Reaction equation

HRID 347518 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=O)[NH:8][CH:7]=[N:6]2.C(N(C(C)C)CC)(C)C.O(Cl)[Cl:22].[P+3].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:22][C:9]1[C:10]2=[C:2]([Cl:1])[CH:3]=[CH:4][N:5]2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 1357420865-Chloropyrrolo[2,1-f][1,2,4]triazin-4(1H)-oneHCID 178479710HCID 178479710, compound

Product 1

HCID 210816694,5-Dichloropyrrolo[2,1-f][1,2,4]triazineYield 67.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-chloropyrrolo[2,1-f][1,2,4]triazin-4 (3H)-one (5.00 g, 29.5 mmol) in toluene (100 mL) at rt under nitrogen was added diisopropylethylamine (5.14 mL, 29.5 mmol) followed by phosphorus(III) oxychloride (8.25 mL, 88.5 mmol). The mixture was heated at 100° C. for 20 h and was then cooled to rt. The reaction was slowly added to saturated aqueous sodium bicarbonate solution (500 mL) at 0° C. After the addition was complete, the mixture was stirred at rt for 30 min. The aqueous phase was extracted with ethyl acetate (3×500 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (3.73 g, 67%) as a yellow solid which was used without further purification. 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.70 (d, 1H, J=2.8 Hz), 6.84 (d, 1H, J=2.8 Hz); MS(ESI+) m/z 188.1 (M+H)+.

Workup

  1. temperaturewas then cooled to rt
  2. additionAfter the addition
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×500 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08333b9b45ba46709d9cde206028d605
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Linked notes

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