1-Butanol → 2-butoxy-9H-purin-6-amine

HRID 2111655Notes

Reaction equation

HRID 2111655 reaction equation
[Na].[CH2:2]([OH:6])[CH2:3][CH2:4][CH3:5].Cl[C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([NH2:17])[N:9]=1>O>[CH2:2]([O:6][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([NH2:17])[N:9]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 949042-ChloroadenineHCID 5360545Sodium2×

Product 1

HCID 229289002-butoxy-9H-purin-6-amineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

Sodium (13.6 g, 0.59 mol) was added to butanol (480 ml), the temperature of the mixture was raised to 90° C. to completely dissolve sodium therein. Subsequently, 2-chloroadenine (4.0 g, 23.6 mmol) was added, and the resultant was heated under reflux for 9 hours. After the reaction solution was cooled to 4° C., water (400 ml) was added thereto, and the resultant was vigorously stirred for 30 minutes. The separated layer of butanol was concentrated under reduced pressure, water (400 ml) was added to the residue, and concentrated hydrochloric acid was added dropwide under ice cooling to neutralize the product. The precipitated solid was collected by filtration, the resulting solid was added to ethanol (70 ml), and the resultant was heated under reflux for 30 minutes. The product was cooled to room temperature, and the precipitated solid was then collected by filtration. Thus, 3.72 g of the title compound was obtained (yield: 76%).

Workup

  1. temperaturethe resultant was heated
  2. temperatureunder reflux for 9 hours
  3. concentrationThe separated layer of butanol was concentrated under reduced pressure, water (400 ml)
  4. additionwas added to the residue, and concentrated hydrochloric acid
  5. additionwas added dropwide under ice cooling
  6. filtrationThe precipitated solid was collected by filtration
  7. additionthe resulting solid was added to ethanol (70 ml)
  8. temperaturethe resultant was heated
  9. temperatureunder reflux for 30 minutes
  10. temperatureThe product was cooled to room temperature
  11. filtrationthe precipitated solid was then collected by filtration

Sources & evidence

ORD record
ord-3603f4001d8e4ea7b746243e291ac767
Source dataset
uspto-grants-2009_04
Patent number
US07521454B2

Reaction notes

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