Sodium Iodide → (S)-5-Methyl-2-(1-((5-(6-oxo-1,6-dihydropyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052705Notes

Reaction equation

HRID 1052705 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:37][C:34]1[CH:35]=[CH:36][N:23]2[C:24]=1[C:25](=[O:33])[N:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]([C@@H:19]([NH:18][C:16]1[C:17]3[C:9]([C:7]4[NH:8][C:3](=[O:2])[CH:4]=[CH:5][CH:6]=4)=[CH:10][NH:11][C:12]=3[N:13]=[CH:14][N:15]=1)[CH3:20])=[N:22]2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 73776365(S)-2-(1-((5-(6-Methoxypyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73775548(S)-5-Methyl-2-(1-((5-(6-oxo-1,6-dihydropyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 41.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

(S)-2-(1-((5-(6-Methoxypyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (22 mg, 0.02 mmol) was dissolved in 440 μl acetonitrile. Sodium iodide (35 md, 0.24 mmol) and chlorotrimethylsilane (30 μl, 0.24 mmol) were added. The reaction mixture was stirred at 40° C. for 8 h. The mixture was poured into 10 mL of sodium bicarbonate solution and extracted twice with ethyl acetate. The organics were dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified using SP1® purification system (0% to 10%, dichloromethane-2-propanol) to give 4 mg (34% yield) of the title compound as a solid. Purity 93%.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organics were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. customSP1® purification system (0% to 10%, dichloromethane-2-propanol)

Sources & evidence

ORD record
ord-a3c33e5223af4a0da4115d9e8d4e68d6
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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