1-Butanol → 2-butoxy-9H-purin-6-amine

HRID 2354826Notes

Reaction equation

HRID 2354826 reaction equation
[Na].Cl[C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5]([NH2:12])[N:4]=1.O.[CH2:14]([OH:18])[CH2:15][CH2:16][CH3:17]>>[CH2:14]([O:18][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5]([NH2:12])[N:4]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 962WaterHCID 949042-ChloroadenineHCID 5360545Sodium

Product 1

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

Conditions

Temperature
140 °C

Procedure

After sodium (13.56 g, 590 mmol) was dissolved in n-butanol (480 ml), 2-chloroadenine (4.0 g, 23.59 mmol) was added thereto and the mixture was stirred at 140° C. for 19 hours. After the mixture was allowed to cool, water (400 ml) was added thereto and the mixture was stirred for 30 minutes. And then the organic layer was separated and concentrated. Water (400 ml) was added to the residue and the solution was neutralized with concentrated hydrochloric acid. The resulting precipitate was filtered and washed with ethanol to give the captioned compound (3.72 g, 17.97 mmol, yield 76%) as a white solid.

Workup

  1. temperatureto cool
  2. stirringthe mixture was stirred for 30 minutes
  3. customAnd then the organic layer was separated
  4. concentrationconcentrated
  5. additionWater (400 ml) was added to the residue
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-859e78c279ea4266b2cb4329a91344d3
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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