9-(2-cyclohexenyl)-2-propoxy-9H-adenine → 9-Cyclohexyl-2-n-propoxy-9H-adenine

HRID 427008Notes

Reaction equation

HRID 427008 reaction equation
[CH:1]1([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([O:17][CH2:18][CH2:19][CH3:20])=[N:11][C:12]=3[NH2:16])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1>C(O)C>[CH:1]1([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([O:17][CH2:18][CH2:19][CH3:20])=[N:11][C:12]=3[NH2:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 127778309-(2-cyclohexenyl)-2-propoxy-9H-adenine

Product 1

HCID 518149-Cyclohexyl-2-n-propoxy-9H-adenine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.21 g. (7.8 mmoles) of 9-(2-cyclohexenyl)-2-n-propoxy-9H-adenine in 30 ml. of 90% ethanol was hydrogenated overnight with 250 mg. of 10% Pd-C and then filtered. The filtrate was evaporated in vacuo, giving a residue which was crystallized from ethyl acetate-n-hexane. Yield 1.85 g. (76%); m.p. 148°-150° C. IR(KBr): 3510, 2930, 1670, 1640, 1595, 1405 cm-1. UV: λmaxMeOH 252 nm (ε 8360), 269 nm (ε 13200). NMR(CDCl3): δ 1.03(3H, t, J=7 Hz), 1.80(12H, m), 4.20(2H, t, J=7 Hz), 4.35(1H, m), 6.02(2H, s), 7.55(1H, s).

Workup

  1. filtrationof 10% Pd-C and then filtered
  2. customThe filtrate was evaporated in vacuo
  3. customgiving a residue which
  4. customwas crystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-fd1b2a8124f84dc6975474a22718cf92
Source dataset
uspto-grants-1979_10
Patent number
US04172829

Reaction notes

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