Methanol → HCID 53740777, compound

HRID 1647186Notes

Reaction equation

HRID 1647186 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:20][O:21][CH3:22])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[H-].[Na+].[CH3:25][OH:26]>>[CH3:25][O:26][C:2]1[N:3]=[C:4]([NH:20][O:21][CH3:22])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 10042350HCID 10042350, compound

Product 1

HCID 53740777HCID 53740777, compound

Procedure

2-Chloro-N-methoxyadenosine (Example 8) (0.20 g, 0.60 mmol) was added to a mixture of sodium hydride (40 % oil dispersion) (0.12 g, 3.0 mmol) methanol (0.24 ml) amd DMF (5 ml) which had been stirred under nitrogen at room temperature for 1 h. The reaction mixture was heated at 80° C. for 16 h, cooled and evaporated. Flash chromatography provided the title 2,N-dimethoxyadenosine, still however containing some starting 2-chloro-N-methoxyadenosine. 1H NMR (DMSO-d6)γ 3.52-3.59 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.77 (3H, s, --OCH3), 3.97 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.60 (1H, q, H-2'), 5.09 (1H, t, 5'-OH), 5.18, 5.44 (2H, 2d, 2' - and 3'-OH), 5.83 (1H, d, H-1'), 8.24 (1H, s, H-8), 11.04 (1H, s, N-H) (desired product only quoted).

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 16 h
  2. temperaturecooled
  3. customevaporated

Sources & evidence

ORD record
ord-750dcdd9617543a9b5efcdf7616891db
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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