9-(2-Cyclohexenyl)-2-ethoxy-9H-adenine → HCID 12777840, compound

HRID 1395071Notes

Reaction equation

HRID 1395071 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][CH3:19])=[N:11][C:12]=3[NH2:16])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1>C(O)C.[Pd]>[CH2:18]([O:17][C:10]1[N:9]=[C:8]2[C:13]([N:14]=[CH:15][N:7]2[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[C:12]([NH2:16])[N:11]=1)[CH3:19]

Participants

4

Reactant 1

HCID 127778299-(2-Cyclohexenyl)-2-ethoxy-9H-adenine

Product 1

HCID 12777840HCID 12777840, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 9-(2-cyclohexenyl)-2-ethoxy-9H-adenine (0.5 mmole) and 10% palladium-on-charcoal (35 mg.) in ethanol (6 ml.) was hydrogenated at room temperature and under atmospheric pressure. The reaction mixture was filtered and the filtrate was evaporated. The residue was lyophilized to give the title product in 40% yield; m.p. 134°-136° C. IR(KBr): 3280, 2995, 1705, 1615, 1525, 1415, 1310, 1010 cm-1. UV: λmaxEtOH 253 nm (ε6800), 269 nm (ε, 10200). NMR(CDCl3): 1.44(3H, t, J=7 Hz), 2.00 (10H, m), 4.45(2H, q, J=7 Hz), 4.50(1H, m), 8.07(1H, s), 8.60(2H, s).

Workup

  1. customwas hydrogenated at room temperature and under atmospheric pressure
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2b222862854b42df9d070b8ec8c9e7e9
Source dataset
uspto-grants-1980_05
Patent number
US04201860

Reaction notes

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