Hydrochloric Acid → 9-(2-Cyclohexenyl)-2-ethoxy-9H-adenine

HRID 427009Notes

Reaction equation

HRID 427009 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]2)=[C:4]([NH2:17])[N:3]=1.[O-:18][CH2:19][CH3:20].[Na+].Cl>C(O)C>[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([O:18][CH2:19][CH3:20])=[N:3][C:4]=3[NH2:17])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 127778182-chloro-9-(2-cyclohexenyl)-9H-adenine

Product 1

HCID 127778299-(2-Cyclohexenyl)-2-ethoxy-9H-adenineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-9-(2-cyclohexenyl)-9H-adenine (310 mg., 1.24 mmole) and a solution of sodium ethoxide in ethanol (0.25-1 N, ~10 ml.) was refluxed overnight under an atmosphere of nitrogen. The reaction mixture was poured into ice-water, neutralized with 1 N HCl and extracted with ethyl acetate (20 ml.). The extracts were washed with water, dried over Na2SO4 and filtered. The filtrate was evaporated and the residue then subjected to silica gel chromatography (silica gel 7 g., eluted with 1% CH3OH-CHCl3) to give the title product in 92% yield; m.p. 67°-72° C. IR(KBr): 3320, 2940, 1640, 1595, 1465, 1410, 1385, 1340 cm-1. UV: λmaxEtOH 254 nm (ε 8400), 269 nm (ε 12600). NMR(CDCl3): 1.44 (3H, t, J=7 Hz), 2.00(6H, m), 4.45(2H, q, J= 7 Hz), 5.20(1H, m), 5.95(2H, m), 6.16(2H, s), 7.62(1H, s).

Workup

  1. extractionextracted with ethyl acetate (20 ml.)
  2. washThe extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. washthe residue then subjected to silica gel chromatography (silica gel 7 g., eluted with 1% CH3OH-CHCl3)

Sources & evidence

ORD record
ord-e18605e6751048c296eef22acf15bbe9
Source dataset
uspto-grants-1979_10
Patent number
US04172829

Reaction notes

Loading…