Sodium Methoxide → 2-Amino-9-[3-(methoxymethoxy)propoxy]purine

HRID 1655936Notes

Reaction equation

HRID 1655936 reaction equation
C([NH:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[O:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][O:19][CH3:20])=[CH:6][N:5]=1)=O.C[O-].[Na+]>CO>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[O:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][O:19][CH3:20])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15228823HCID 15228823, compound

Product 1

HCID 103775662-Amino-9-[3-(methoxymethoxy)propoxy]purineYield 55.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-formamido-9-[3-(methoxymethoxy)propoxy]purine (0.4 g, 1.42 mmol) in methanol (15 ml) was treated with sodium methoxide solution (0.5M, 5 ml) and heated to reflux for 2 hr. The cooled reaction mixture was neutralised with AMBERLITE IR 120H resin, filtered and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (50 ml), washed with water (2×20 ml), dried (MgSO4), filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica eluting with ethyl acetate, followed by crystallisation from acetone/hexane to give the title compound as colourless crystals (0.2 g, 55%) mp 80°-1° C. λmax (MeOH) 223 (ε26,375), 245 (5020) and 310 nm (7320); νmax (KBr) 3320, 3180, 3080, 2940, 2880, 1645, 1610, 1580, 1505, 1465, and 1430 cm-1 ; δH [(CD3)2SO] 1.95 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.25 (3H, s, OCH3), 3.63 (2H, t, J=6.3 Hz, CH2OCH2OCH3), 4.40 (2H, t, J=6.3 Hz, CH2ON), 4.57 (2H, s, OCH2O), 6.68 (2H, br.s, D2O exchangeable NH2), 8.3 (1H, s, 8-H), 8.59 (1H, s, 6-H). (Found: C, 47.34, H 6.08% C10H15N5O3 requires: C, 47.42; H, 59.7%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hr
  3. customThe cooled reaction mixture
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  7. washwashed with water (2×20 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe filtrate evaporated in vacuo
  11. customThe residue was purified by column chromatography on silica eluting with ethyl acetate
  12. customfollowed by crystallisation from acetone/hexane

Sources & evidence

ORD record
ord-8d38f6e3f1504b01847c9187250b5913
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

Loading…