Potassium Carbonate → (S)-5-Methyl-2-(1-((6-methylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052700Notes

Reaction equation

HRID 1052700 reaction equation
Br[C:2]1[S:30][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C@H:11]([C:13]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17](=[O:25])[C:16]4=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]4[N:14]=3)[CH3:12])[C:4]=2[CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.[Cl-].[NH4+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][C:26]1[CH:27]=[CH:28][N:15]2[C:16]=1[C:17](=[O:25])[N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([C@@H:11]([NH:10][C:9]1[C:4]3[CH:3]=[C:2]([CH3:31])[S:30][C:5]=3[N:6]=[CH:7][N:8]=1)[CH3:12])=[N:14]2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 574072TrimethylboroxineHCID 118433746(S)-2-(1-((6-Bromothieno[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 73776064(S)-5-Methyl-2-(1-((6-methylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

(S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.10 mmol) was dissolved in 3 mL dimethylformamide. Potassium carbonate (287 mg, 2.08 mmol), tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) and trimethylboroxine (130 μl, 0.93 mmol) were added under argon conditions. The reaction mixture was stirred at 130° C. for 2 h. The crude was poured into 25 mL saturated ammonium chloride solution and extracted twice with ethyl acetate. The organics were dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System by reverse phase to obtain 26 mg (60% yield) of a yellow solid as a title compound. Purity 100%.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organics were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified
  6. customSP1® Purification System by reverse phase

Sources & evidence

ORD record
ord-50ef15b0677243fd9ca87d6588badaa6
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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