Hydrazine → 4-hydrazino-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 223160Notes

Reaction equation

HRID 223160 reaction equation
Cl[C:2]1[C:3]2[CH:12]=[CH:11][N:10]([C@@H:13]3[O:33][C@H:32]([CH2:34][O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@@H:23]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:14]3[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.[NH2:43][NH2:44]>C(OCC)(=O)C>[NH:43]([C:2]1[C:3]2[CH:12]=[CH:11][N:10]([C@@H:13]3[O:33][C@H:32]([CH2:34][O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@@H:23]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:14]3[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1)[NH2:44]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 132771774-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 228216904-hydrazino-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 55 g of 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine and 500 ml of anhydrous hydrazine is heated under reflux and a nitrogen atmosphere for two hours, evaporated in vacuo, and coevaporated with xylenes. The residue is distributed between a mixture of ethyl acetate and water and the aqueous layer reextracted with ethyl acetate. The dried ethyl acetate extracts are combined and evaporated in vacuo to provide 51 g of crude syrupy product. Chromatography of this material over silica gel and ethyl acetate provides 49 g of pure 4-hydrazino-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine as a yellow syrup.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. customevaporated in vacuo
  4. additionThe residue is distributed between a mixture of ethyl acetate and water
  5. customevaporated in vacuo
  6. customto provide 51 g of crude syrupy product

Sources & evidence

ORD record
ord-ab59dfcd099d4274a48d9431217a9110
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

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