Acetic Acid → 2-Amino-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-6-methoxypurine

HRID 1089269Notes

Reaction equation

HRID 1089269 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]1.[C:24](O)(=[O:26])C>C[O-].[Na+].CO>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]2[CH2:17][O:18][C:19]([CH3:22])([CH3:23])[O:20][CH2:21]2)=[C:2]([O:26][CH3:24])[N:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 221605896-Chloro-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-2-formamidopurine

Product 1

HCID 198136312-Amino-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-6-methoxypurineYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10942334Sodium MethoxideSolvent

Procedure

6-Chloro-9-(2,2-dimethyl-1,3-dioxan-5-ylmethoxy)-2-formamidopurine (0.5 g, 1.46 mmol) in 1.2M sodium methoxide in methanol (3.38 ml) and methanol (5 ml) was heated at reflux temperature for 1.5 hours and then cooled. Acetic acid (0.16 ml) was added and the solution evaporated to dryness. The residue was suspended in water and extracted with ethyl acetate (2×50 ml). The combined ethyl acetate extracts were washed with water, dried (magnesium sulphate) and evaporated under reduced pressure. Chromatography on silica gel (eluted with chloroform-ethanol, 100:1) gave the title compound (310 mg, 69%). 1R: υmax (KBr) 3397, 3208, 1640, 1616, 1581, 1480, 1390 cm-1. 1H NMR: δH [(CD3)2SO] 1.32(3H,s,CH3), 1.35(3H,s,CH3), 2.00(1H,m,CH), 3.77(2H,dd, J=11.8, 6.1 Hz, 2×H(ax), 3.9 (3H,s,OCH3), 3.99 (2H,dd,J=11.8, 4.1 Hz, 2×H(eq)), 4.36(2H,d, J=6.8 Hz, CH2ON), 6.60(2H,br.s, D2O exchangeable, NH2), 8.14(1H,s,H-8). Found: C, 49.30; H, 6.12; N, 22.03%; M+ 309.1455. C13H19N5O4 0.5H2O requires: C, 49.04; H, 6.34; N, 22.00%; M+ 309.1437.

Workup

  1. temperatureat reflux temperature for 1.5 hours
  2. temperaturecooled
  3. customthe solution evaporated to dryness
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe combined ethyl acetate extracts were washed with water
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-39dcd7cbc1584e38af7475f4231bde4a
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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