Potassium Carbonate → HCID 86679631, compound

HRID 577687

Reaction equation

HRID 577687 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4](Cl)[N:3]=1.[OH:20][C:21]1[CH:22]=[C:23]([NH:27][C:28](=[O:31])[CH:29]=[CH2:30])[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([O:20][C:21]2[CH:22]=[C:23]([NH:27][C:28](=[O:31])[CH:29]=[CH2:30])[CH:24]=[CH:25][CH:26]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 275403n-(3-Hydroxyphenyl)acrylamideHCID 582852322,6-Dichloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

Product 1

HCID 86679631HCID 86679631, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,6-dichloro-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine (1.78 g, 5.58 mmol) and N-(3-hydroxyphenyl)prop-2-enamide (1.00 g, 6.13 mmol) in DMF (28 mL) was added K2CO3 (2.34 g, 16.7 mmol). The reaction was heated to 60° C. for 30 min, at which point LCMS showed consumption of starting material. The mixture was cooled to rt and partitioned between water and EtOAc. The layers were separated, and the aqueous layer was extracted with EtOAc twice more. The combined organics were washed with water (three times) and brine, dried over Mg2SO4, and filtered. The filtrate was concentrated, and the crude material was purified by flash chromatography on a Biotage 40M column; product was eluted with 0%-40% EtOAc/heptane to yield the title compound (2.10 g, 85% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.35 (s, 1H) 8.69 (s, 1H) 7.74 (t, J=2.02 Hz, 1H) 7.50-7.56 (m, 1H) 7.41-7.48 (m, 1H) 7.05 (ddd, J=7.96, 2.27, 0.88 Hz, 1H) 6.39-6.50 (m, 1H) 6.22-6.32 (m, 1H) 5.75-5.81 (m, 1H) 5.62 (s, 2H) 3.57-3.66 (m, 2H) 0.84-0.91 (m, 2H) −0.05 (s, 9H). m/z (APCI+) for C20H24ClN5O3Si 446.00 (M+H)+.

Workup

  1. customconsumption of starting material
  2. temperatureThe mixture was cooled to rt
  3. custompartitioned between water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc twice more
  6. washThe combined organics were washed with water (three times) and brine
  7. dry with materialdried over Mg2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customthe crude material was purified by flash chromatography on a Biotage 40M column
  11. washproduct was eluted with 0%-40% EtOAc/heptane

Sources & evidence

ORD record
ord-78a285906c6c4b8cbc82bc3e992d5f8e
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Linked notes

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