Ammonia → 2',3'-Didehydro-2',3'-dideoxyguanosine

HRID 2209759Notes

Reaction equation

HRID 2209759 reaction equation
N#N.C([C@@:8]1([N:15]2[C:25]3[N:24]=[C:22]([NH2:23])[NH:21][C:19](=[O:20])[C:18]=3[N:17]=[CH:16]2)[O:14][C@H:11]([CH2:12][OH:13])[CH:10]=[CH:9]1)(=O)C(C)C.N>CO>[C@@H:8]1([N:15]2[C:25]3[N:24]=[C:22]([NH2:23])[NH:21][C:19](=[O:20])[C:18]=3[N:17]=[CH:16]2)[O:14][C@H:11]([CH2:12][OH:13])[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 136375549HCID 136375549, compound

Product 1

HCID 1354742232',3'-Didehydro-2',3'-dideoxyguanosineYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 27 (0.3 g, 0.94 mmol) in methanol saturated with ammonia (20 ml) was stirred at 50°-55° C. for 12 hours in a pressure vessel. The reaction mixture was cooled to room temperature. The solid obtained was filtered, washed with cold isopropanol, and dried. Crystallization from methanol afforded 0.2 g (81%) of 9 as an amorphous solid: mp >250° C.; UV (methanol) λmax (pH 1) 270 mn, 251; (pH 7) 269 (sh), 255; (pH 11) 268; 1H NMR (DMSO-d6) 63.48-3.59 (2H, m, 5'-H), 4.70-5.00 (2H, m, 4'-H and OH), 6.08 (1H, br d, J=5.93 Hz, 2'-H), 6.40-6.47 (3H, m, 3'-H and NH2), 6.68 (1H, m, 1'-H), 7.70 (1H, s, 8-H).

Workup

  1. customThe solid obtained
  2. filtrationwas filtered
  3. washwashed with cold isopropanol
  4. customdried
  5. customCrystallization from methanol

Sources & evidence

ORD record
ord-290b6f75c1f7400eabcf0afbf7c5f870
Source dataset
uspto-grants-1995_10
Patent number
US05455339

Reaction notes

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