Ammonia → 9-(2-Hydroxypropyl)adenine

HRID 27586Notes

Reaction equation

HRID 27586 reaction equation
[OH:1][CH:2]([CH3:14])[CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2Cl.[NH3:15]>[Cl-].[NH4+]>[OH:1][CH:2]([CH3:14])[CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2[NH2:15]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 120651829-(2-Hydroxy-1-propyl)-6-chloropurine

Product 1

HCID 19429-(2-Hydroxypropyl)adenine

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

9-(2-Hydroxy-1-propyl)-6-chloropurine (I, 9 g, 42.5 mmol) was dissolved in saturated methanolic ammonia and ammonium chloride (50 mg). The mixture was heated at 130° in a bomb for 6 hr. The resulting solution was evaporated to dryness and recrystallized from ethanol/acetone. Yield=6.68 g of a colorless crystalline product (81%); mp 193°-194°; uv (H2O; pH 5.5); λmax 260 nm; TLC in CHCl3 :MeOH (5:1); Rf 0.44.

Workup

  1. temperatureThe mixture was heated at 130° in a bomb for 6 hr
  2. customThe resulting solution was evaporated to dryness
  3. customrecrystallized from ethanol/acetone

Sources & evidence

ORD record
ord-00631e75d90f45969f8128c2aee8fc19
Source dataset
uspto-grants-1980_09
Patent number
US04221909

Reaction notes

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