Potassium Carbonate → HCID 178450377, compound

HRID 1684974Notes

Reaction equation

HRID 1684974 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:25]C)[N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)=[C:8]([NH2:27])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1>CN(C=O)C>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([OH:25])[N:12]2[CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([O:24][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[O:23])=[CH:20][CH:21]=2)=[C:8]([NH2:27])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 23079437HCID 23079437, compound

Product 1

HCID 178450377HCID 178450377, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 2-butoxy-9-(4-carboxybenzyl)-8-methoxyadenine (0.05 g, 0.13 mmol) prepared in accordance with the method of Reference example 5 and potassium carbonate (0.03 g, 0.22 mmol) were added to DMF (10 ml), 3-chloromethylpyridine hydrochloride (0.03 g, 0.18 mmol) was added thereto, and the mixture was stirred at room temperature for 18 hours. After removing the solvent, the residue was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=300/1˜30/1) and the resulting solid was added to methanol (10 ml) and concentrated hydrochloric acid (10 ml). The mixture was stirred at room temperature for 18 hours. After being neutralized with saturated sodium hydrogencarbonate, the solution was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, concentrated and washed with methanol to give the captioned compound (0.03 g, 0.07 mmol, yield: 52%) as a white solid.

Workup

  1. additionwas added
  2. customAfter removing the solvent
  3. additionthe residue was poured into water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=300/1˜30/1)
  8. additionthe resulting solid was added to methanol (10 ml) and concentrated hydrochloric acid (10 ml)
  9. stirringThe mixture was stirred at room temperature for 18 hours
  10. extractionthe solution was extracted with dichloromethane
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated
  13. washwashed with methanol

Sources & evidence

ORD record
ord-c11229bd9a3f4d6f9583b7c551a383b4
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Reaction notes

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