Sodium Carbonate → HCID 89630028, compound

HRID 882166Notes

Reaction equation

HRID 882166 reaction equation
Br[C:2]1[C:10]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.[O:28]1[CH2:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.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>[O:28]1[CH2:29][CH:30]=[C:31]([C:2]2[C:10]3[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=4)=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=2)[CH2:32][CH2:33]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 89630012HCID 89630012, compound

Product 1

HCID 89630028HCID 89630028, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 2.23 mmol) in toluene/EtOH/H2O (4:2:1, 14 mL), was added 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.70 g, 3.3 mmol), sodium carbonate (0.70 g, 6.7 mmol) and Pd(PPh3)4 (0.13 g, 0.11 mmol). The resulting solution was stirred for 12 hours at 80° C., cooled, and quenched by the addition of water (50 mL). The resulting solution was extracted with ethyl acetate (×3) and the organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 1-50% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 5-(3,6-dihydro-2H-pyran-4-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine as a yellow solid. LRMS (ESI) calc'd for C23H29N4O4Si [M+H]+: 453, found 453.

Workup

  1. temperaturecooled
  2. customquenched by the addition of water (50 mL)
  3. extractionThe resulting solution was extracted with ethyl acetate (×3)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe reaction was then purified by chromatography
  9. washeluting with 1-50% EtOAc/petroleum ether
  10. customThe product was collected
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cffb70b2d82d4131a32d8f3234ef9333
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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