Sodium Hydroxide → HCID 19763330, compound

HRID 248321Notes

Reaction equation

HRID 248321 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12][C:13]([O:15]C)=[O:14].[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19763329HCID 19763329, compound

Product 1

HCID 19763330HCID 19763330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 10.4 g (0.0432 mol) of 6-chloro-9-(2-carbomethoxyethyl)purine in 400 mL dioxane, 20 mL H2O and 50 mL N NaOH was stirred 2 h at room temperature. Nearly all the solvent was removed by roto-evaporation and 50 mL of N HCl was added. The mixture was chilled and the precipitate collected; 9.00 g (92%); recrystallized from methanol-petroleum ether; mp 163°-165°; 1H NMR (200 MHz, DMSO-d6) δ8.80 (1H, s, 7 or 8-H), 4.52(2H, t), 2.97 (2H, t, CH2CO).

Workup

  1. customNearly all the solvent was removed by roto-evaporation and 50 mL of N HCl
  2. additionwas added
  3. temperatureThe mixture was chilled
  4. customthe precipitate collected
  5. customrecrystallized from methanol-petroleum ether

Sources & evidence

ORD record
ord-76f702d27336449fa4c5167475c0dd82
Source dataset
uspto-grants-1993_05
Patent number
US05210077

Reaction notes

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