Sodium Carbonate → HCID 131736212, compound

HRID 1052587Notes

Reaction equation

HRID 1052587 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=1.[Si:39]([O:46][CH2:47][CH2:48][CH2:49][N:50]1[CH:54]=[C:53](B2OC(C)(C)C(C)(C)O2)[CH:52]=[N:51]1)([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Si:39]([O:46][CH2:47][CH2:48][CH2:49][N:50]1[CH:54]=[C:53]([C:2]2[C:10]3[C:9]([NH:11][C@H:12]([C:14]4[N:19]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:18](=[O:26])[C:17]5=[C:27]([CH3:30])[CH:28]=[CH:29][N:16]5[N:15]=4)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:3]=2)[CH:52]=[N:51]1)([C:42]([CH3:45])([CH3:43])[CH3:44])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 89447085HCID 89447085, compoundHCID 131736122(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-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 131736212HCID 131736212, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (120 mg, 0.2 mmol) was treated with 1-(3-(tert-butyldimethylsilyloxy)propyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (180 mg, 0.49 mmol), tetrakistriphenylphosphine palladium (72 mg, 0.06 mmol) and aqueous solution of sodium carbonate (2M, 250 μl, 0.5 mmol) in DMF (3 ml). The reaction mixture was submitted at vacuum-argon cycles and stirred at 100° C. for 3 h. The reaction mixture was cooled down to room temperature and poured over ice, basified with potassium carbonate and extracted with ethyl acetate (×3). The organic phase was successively washed with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. The residue was purified by normal phase using SP1® Purification System (0% to 50%, hexane-diethyl ether) to obtain 124 mg (69% yield) of the title compound. Purity: 85%.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. additionpoured over ice
  3. extractionextracted with ethyl acetate (×3)
  4. washThe organic phase was successively washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue was purified by normal phase
  9. custom® Purification System (0% to 50%, hexane-diethyl ether)

Sources & evidence

ORD record
ord-7550d8d29b3d498d830cc62b2e6a201d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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