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

HRID 427010Notes

Reaction equation

HRID 427010 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(ε 6800), 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-d0320dea5cc8424cbef8760876b6c53e
Source dataset
uspto-grants-1979_10
Patent number
US04172829

Reaction notes

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