1-Propanol → Purine, 2-amino-6-propoxy-

HRID 465709Notes

Reaction equation

HRID 465709 reaction equation
[Na].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5](Cl)[N:4]=1.[CH2:13]([OH:16])[CH2:14][CH3:15]>>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5]([O:16][CH2:13][CH2:14][CH3:15])[N:4]=1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 53603492-Amino-6-chloropurineHCID 5360545Sodium

Product 1

HCID 95802Purine, 2-amino-6-propoxy-

Conditions

Temperature
85 °C

Procedure

Sodium (0.68 g, 29.5 mmol Aldrich lot #9621CL) was added in portions to anhydrous propanol (25 mL). Upon complete dissolution 2-amino-6-chloropurine (1 g, 5.9 mmol, Sigma lot #69F4064) was added and the reaction heated in an 85° C. oil bath under a nitrogen atmosphere for 20 hours. The solution was cooled and neutralized with Dowex 50W×12 (H+ form) (BioRad, 140-270 mesh), an acidic ion exchange resin. The resin was filtered, the filtrate collected and adsorbed onto silica gel column and eluted with CHCl3 /MeOH (9:1, v/v). Combination and evaporation of appropriate fractions gave 0.89 g of slightly impure material. Adsorption of this material onto silica gel followed by elution with EtOAc/MeOH (10:1, v/v) gave, after evaporation of combined product fractions, 0.76 g, (3.9 mmol; 67%). mp=198°-200° C.

Workup

  1. additionwas added
  2. temperatureThe solution was cooled
  3. filtrationThe resin was filtered
  4. customthe filtrate collected
  5. washeluted with CHCl3 /MeOH (9:1
  6. customCombination and evaporation of appropriate fractions
  7. customgave 0.89 g of slightly impure material
  8. washAdsorption of this material onto silica gel followed by elution with EtOAc/MeOH (10:1
  9. customv/v) gave
  10. customafter evaporation of combined product fractions, 0.76 g, (3.9 mmol; 67%)

Sources & evidence

ORD record
ord-f961f64449b847eea6bb55ac822a0b69
Source dataset
uspto-grants-1992_10
Patent number
US05153318

Reaction notes

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