Triethylamine → HCID 22854551, compound

HRID 1901519Notes

Reaction equation

HRID 1901519 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([NH2:29])=[N:23][C:24]=2Cl)(=[O:3])[CH3:2].[NH2:30][N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(CC)CC)C>O1CCOCC1>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:20]2[N:21]=[C:22]([NH2:29])[N:23]=[C:24]([NH:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:25]=2[N:26]=[CH:27]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166581-AminopiperidineHCID 10788628(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Product 1

HCID 22854551HCID 22854551, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9-(2',3',5'-Tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloro-(9H)-purine (6.0 g, 14 mmol) (prepared as described by Robins, M. J. and Uznanski, B., in Nucleic Acid Chemistry (Townsend, L. B. and Tipson, R. S., eds.,) John Wiley and Sons, Inc., 1986, 3, 144) was dissolved in dioxan (100 ml). 1-Aminopiperidine (1.83 ml, 16.95 mmol) was added followed by triethylamine (2.33 ml, 18.5 mmol) and the solution was stirred for 190 hours at room temperature. The reaction mixture was filtered, evaporated and the resultant residue was purified by column chromatography on silica gel eluting with ethyl acetate/cyclobexane (3/1) to afford 2',3',5'-tri-O-acetyl-2-amino-N-(1-piperidinyl)adenosine (4.88 g, 71%) as a foam which solidified on coevaporation with methanol: m.p. 77°-790° C. 1H NMR (400 MHz, Me2SO-d6) δ 2.04 (6H, s, 2' and 3'-O-acetyl-CH3), 2.13 (3H, s, 5'-O-acetyl-CH3), 4.30 (2H, m, H-5'a and H-4'), 4.40 (1H, dd, H-5'b), 6.03 (1H, d, H-1').

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customthe resultant residue was purified by column chromatography on silica gel eluting with ethyl acetate/cyclobexane (3/1)

Sources & evidence

ORD record
ord-e64d9033c0d343efbd809ae22d81c0d0
Source dataset
uspto-grants-1996_11
Patent number
US05578582

Reaction notes

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