Sodium ethoxide → HCID 22160550, compound

HRID 1089249Notes

Reaction equation

HRID 1089249 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([NH:23]C=O)=[N:17][C:18]=2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:26][CH2:27][CH3:28].[Na+]>C(O)C>[NH2:23][C:16]1[N:15]=[C:14]2[C:19]([N:20]=[CH:21][N:13]2[O:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:18]([O:26][CH2:27][CH3:28])[N:17]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 13989894HCID 13989894, compound

Product 1

HCID 22160550HCID 22160550, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9-(3-benzyloxyprop-1-oxy)-6-chloro-2-formamidopurine (500 mg, 1.38 mmol) in 0.4M sodium ethoxide in ethanol (10 ml) was heated at 80° C. for 2.5 hours. The mixture was then cooled and evaporated under reduced pressure. The residue was dissolved in water (20 ml) and the solution was brought to pH 7 with dilute hydrochloric acid. The aqueous solution was extracted with chloroform (2×20 ml) and the combined extracts were washed with water (10 ml), dried (magnesium sulphate) and evaporated under reduced pressure. Column chromatography on silica gel (eluted with chloroform-ethanol, 50:1) yielded the title compound (390 mg, 8%). IR: υmax (KBr) 3353, 3217, 1652, 1611, 1579, 1506, 1461, 1445, 1407 cm-1. 1H NMR: δH [(CD3)2SO] 1.35 (3H, t, J=7.2 Hz, CH3CH2O), 1.95 (2H, quintet, J=6.3, 6.6 Hz, CH2CH2CH2), 3.60 (2H, t, 6.3 Hz), 4.37 (2H, t, J=6.6 Hz, CH2ON), 4.42 (2H, quartet, J=7.2 Hz, CH3CH2O), 4.48 (2H, s, CH2Ph), 6.55 (2H, br.s, D2O exchangeable, NH2), 7.33 (5H, m, Ph), 8.07 (1H, s, H-8).

Workup

  1. temperatureThe mixture was then cooled
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water (20 ml)
  4. extractionThe aqueous solution was extracted with chloroform (2×20 ml)
  5. washthe combined extracts were washed with water (10 ml)
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-75d44fb2c28d406a9727d8ac03ae1c52
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

Loading…