Ammonia → 2-Fluoroadenosine

HRID 1451118Notes

Reaction equation

HRID 1451118 reaction equation
N.[F:2][C:3]1[N:4]=[C:5]([NH2:30])[C:6]2[N:7]=[CH:8][N:9]([C:28]=2[N:29]=1)[C@@H:10]1[O:27][C@H:21]([CH2:22][O:23]C(=O)C)[C@@H:16]([O:17]C(=O)C)[C@H:11]1[O:12]C(=O)C>C(O)C>[F:2][C:3]1[N:4]=[C:5]([NH2:30])[C:6]2[N:7]=[CH:8][N:9]([C:28]=2[N:29]=1)[C@@H:10]1[O:27][C@H:21]([CH2:22][OH:23])[C@@H:16]([OH:17])[C@H:11]1[OH:12]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 218162712',3',5'-Tri-O-acetyl-2-fluoroadenosine

Product 1

HCID 89752-FluoroadenosineYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous ammonia was bubbled through a magnetically stirred suspension of 2-fluoro-2',3',5'-tri-O-acetyl-adenosine (2.10 g, 5.1 mmol) in absolute ethanol (500 mL) cooled in an ice-water bath. After 30 min the mixture became homogenous so the addition of ammonia was stopped. The container was tightly stoppered and was stored at 4° C. for days, then the mixture was concentrated under vacuum. The residue was recrystallized twice from ethanol and dried to obtain 1.32 g (90%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 3.5-3.75 (m, 2H), 3.96 (q, 1H), 4.15 (q, 1H), 4.54 (q, 1H), 5.09 (t, 1H), 5.32 (d, 1H), 5.50 (d, 1H), 5.81, (d, 1H), 7.9 (bs, 2H), 8.38 (s, 1H); FT-IR (KBr) 3323, 1688, 1617, 1368 cm-1 ; UV (ethanol) λmax 262 nm.

Workup

  1. temperaturecooled in an ice-water bath
  2. waitwas stored at 4° C. for days
  3. concentrationthe mixture was concentrated under vacuum
  4. customThe residue was recrystallized twice from ethanol
  5. customdried

Sources & evidence

ORD record
ord-6005c2e2fe16453d8efbd3aee1d748ba
Source dataset
uspto-grants-1997_02
Patent number
US05602246

Reaction notes

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