Sodium hydride → HCID 60162033, compound

HRID 243342Notes

Reaction equation

HRID 243342 reaction equation
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[N:5][CH:4]=1.CS(O[CH2:18][C:19]1[O:20][C:21]2[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=2[C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)=O>CN(C=O)C>[C:24]1([C:23]2[C:22]3[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=3[O:20][C:19]=2[CH2:18][N:7]2[CH:8]=[N:9][C:10]3[C:6]2=[N:5][CH:4]=[N:3][C:11]=3[NH2:12])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86668871HCID 86668871, compoundHCID 178508693HCID 178508693, compound

Product 1

HCID 60162033HCID 60162033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of NaH (60% in mineral oil, 18 mg, 0.43 mmol) in DMF (5 mL) at 0° C. was added 9H-purin-6-ylamine (54 mg, 0.397 mmol). After 5 min stirring at 0° C., a solution of methanesulfonic acid 3-phenylbenzofuran-2-ylmethyl ester from Example 25 (100 mg, 0.331 mmol) in DMF (1 mL) was added dropwise and the mixture was slowly warmed to RT and stirred at RT for 2.5 h. The reaction mixture was then quenched by addition of water and diluted with DCM. The organic layer was dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) and triturated form EtOAc with cyclohexane affording 163 as an off-white solid (33 mg, 29%). LCMS: RT 3.85 min [M+H]+ 342.1. 1H NMR (DMSO, 400 MHz): δ 8.21 (1H, s), 8.11 (1H, s), 7.79-7.74 (2H, m), 7.63-7.53 (4H, m), 7.50-7.44 (1H, m), 7.38-7.27 (2H, m), 7.23 (2H, s), 5.65 (2H, s)

Workup

  1. temperaturethe mixture was slowly warmed to RT
  2. stirringstirred at RT for 2.5 h
  3. customThe reaction mixture was then quenched by addition of water
  4. additiondiluted with DCM
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc)
  8. customtriturated form EtOAc with cyclohexane affording 163 as an off-white solid (33 mg, 29%)

Sources & evidence

ORD record
ord-52cea368c73e4b4e9cdcd575e4b24dce
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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