Hydrochloric Acid → HCID 57579070, compound

HRID 881800Notes

Reaction equation

HRID 881800 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25]C)[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21].Cl.[C:28](#N)[CH3:29]>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]([CH2:28][CH3:29])[C:5](=[O:25])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 57579036HCID 57579036, compound

Product 1

HCID 57579070HCID 57579070, compound

Procedure

3-((6-Amino-8-methoxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzonitrile (9) (50 mg) was dissolved in acetonitrile (2 mL). A 6N aqueous HCl solution (2 mL) was added and the mixture was stirred at ambient temperature overnight. After evaporation to dryness, the residue was dissolved in DMF (1 mL). Potassium carbonate (100 mg) and ethyl iodide (0.02 mL) were added and the mixture was stirred at ambient temperature for 5 hours. After dilution with water (20 mL) the product was extracted with dichloromethane. The combined organic layers were washed with water and brine, dried with Na2SO4 and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: 0-10% MeOH in ethyl acetate) gave 3-((6-amino-7-ethyl-2-(2-methoxyethoxy)-8-oxo-7,8-dihydropurin-9-yl)methyl)benzonitrile (10) (35 mg) as a colorless glass.

Workup

  1. customAfter evaporation to dryness
  2. dissolutionthe residue was dissolved in DMF (1 mL)
  3. additionPotassium carbonate (100 mg) and ethyl iodide (0.02 mL) were added
  4. stirringthe mixture was stirred at ambient temperature for 5 hours
  5. extractionAfter dilution with water (20 mL) the product was extracted with dichloromethane
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried with Na2SO4
  8. customevaporated under vacuum
  9. customPurification by flash chromatography on silica gel (eluent: 0-10% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-24b61f2569e44754a332d46a376f1d9e
Source dataset
uspto-grants-2015_03
Patent number
US08993755B2

Reaction notes

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