Water → HCID 135703167, compound

HRID 27580Notes

Reaction equation

HRID 27580 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]=2N.N([O-])=[O:16].[Na+].O>C(O)(=O)C>[OH:1][CH:2]([CH3:14])[CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:9](=[O:16])[NH:8][CH:7]=[N:6][C:5]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 19429-(2-Hydroxypropyl)adenineHCID 23668193Sodium Nitrite

Product 1

HCID 135703167HCID 135703167, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9-(2-Hydroxy-1-propyl)adenine (I, 4.0 g, 20.7 mmol) was suspened in 50% acetic acid (20 ml) and sodium nitrite (4 g, 58 mmol), was slowly added. The mixture was stirred at 25° for 3 hr. The resulting solution was evaporated to dryness and isopropanol added; this operation was repeated once. The solid residue was boiled in isopropanol and filtered. The filtrate was evaporated and crystallized by addition of acetone. Recrystallization was made from iso-propanol/methanol (98:2); a colorless crystalline product was obtained. Yield 3.3 g (82%); M.P. 244°-250°; uv (H2O; pH 5.5), λmax 250 nm.

Workup

  1. customThe resulting solution was evaporated to dryness and isopropanol
  2. additionadded
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customcrystallized by addition of acetone
  6. customRecrystallization
  7. customa colorless crystalline product was obtained

Sources & evidence

ORD record
ord-9e325db5ddec4fedac15f39e5a1f0158
Source dataset
uspto-grants-1980_09
Patent number
US04221910

Reaction notes

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