Triethylamine → HCID 54013946, compound

HRID 1379645Notes

Reaction equation

HRID 1379645 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][NH2:6].[CH:7]1[N:12]=[C:11](Cl)[C:10]2[N:14]=[CH:15][N:16]([C@@H:17]3[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]3[OH:25])[C:9]=2[N:8]=1.C(N(CC)CC)C>O1CCOCC1>[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:11]1[C:10]2[N:14]=[CH:15][N:16]([C:9]=2[N:8]=[CH:7][N:12]=1)[C@@H:17]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]1[OH:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 130007292-Methoxyethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 54013946HCID 54013946, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by the procedure described in example 7 by reacting 2-methoxyethylamine hydrochloride (0.27 g, 3.6 mmol) with 6-chloropurine riboside (i.e. 9-β-D-ribofuranosyl-6-chloro-9H-purine)(1.0 g, 3.5 mmol) in dioxan (30 ml) at room temperature for 72 h with triethylamine (1.04 ml, 7.5 mmol) present. The reaction mixture was filtered and evaporated and the resultant residue was recrystallised from methanol (100 ml) to provide the title compound (0.80 g, 82%) as a solid, mp 151°-152° C., 1H NMR (DMSO-d6)δ 3.26 (3H, s, --CH3), 3.50-3.58 (3H, m, H-5'a and --CH2 --), 3.60-3.70 (3H, m, H-5'b, and --CH2 --), 3.96 (1H, q, H-4'), 4.14 (1H, dd, H-3'), 4.60 (1H, dd, H-2') 5.20, 5.45 (2H, 2d, 2'- and 3'-OH), 5.42 (1H, t, 5'-OH) 5.87 (1H, d, H-1'), 7.80 (1H, br s, --NH) 8.22, 8.35 (2H, 2s, H-2 and H-8).

Workup

  1. customThe title compound was prepared by the procedure
  2. customat room temperature
  3. customfor 72 h
  4. filtrationThe reaction mixture was filtered
  5. customevaporated
  6. customthe resultant residue was recrystallised from methanol (100 ml)

Sources & evidence

ORD record
ord-0bd8071e0a8141caaf084ad7c1d9eb5e
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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