Bromine → HCID 86592810, compound

HRID 2216256Notes

Reaction equation

HRID 2216256 reaction equation
[I:1][C:2]1[N:3]=[C:4]([NH2:20])[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].[Br:21]Br.OS([O-])=O.[Na+]>CC([O-])=O.[Na+]>[I:1][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[C:7]([Br:21])[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

5

Reactant 3

HCID 24408BromineHCID 1696622-IodoadenosineHCID 23665763Sodium Bisulfite

Product 1

HCID 86592810HCID 86592810, compound

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Procedure

2-Iodoadenosine (1, 2.93 g, 7.45 mmol) was dissolved in NaOAc buffer (1.0 M, pH 4, 50 ml) at 50° C. The solution was cooled to room temperature and bromine (0.46 mL, 8.94 mmol) was added. After stirring overnight at room temperature, adding NaHSO3 destroyed the excess of bromine and the pH of the solution was adjusted to 7 with NaOH solution (5 M). The reaction mixture was kept at 4° C. for 5 hr and the precipitate was filtered. The white solid was washed with water and dried. Yield 2.43 mg (5.14 mmol, 69%), Rƒ 0.69 (10% MeOH in EtOAc); 1H NMR (DMSO-d6) δ 7.91 (s, 2H, NH2), 5.77 (d, 1H, J=6.52 Hz, H-1′), 5.47 (d, 1H, J=5.84 Hz, OH-2′), 5.24 (d, 1H, J=4.80 Hz, OH-5′), 5.03–4.84 (m, 2H, OH-3′, H-2′), 4.20–4.09 (m, 1H, H-3′), 3.97–3.88 (m, 1H, H-4′), 3.71–3.42 (m, 2H, H-5′) ppm.

Workup

  1. customdestroyed the excess of bromine
  2. waitThe reaction mixture was kept at 4° C. for 5 hr
  3. filtrationthe precipitate was filtered
  4. washThe white solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-e7fba826e0b44033827d2c41683af3ae
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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