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

HRID 1904112Notes

Reaction equation

HRID 1904112 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C@@H:21]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@@H:12]3[O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:41][NH2:42]>>[NH:41]([C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C@@H:21]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@@H:12]3[O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[N:5]=[CH:6][N:7]=1)[NH2:42]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 544305474-chloro-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 541466234-hydrazino-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Procedure

A mixture of 10 g of 4-chloro-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine and 100 ml of anhydrous hydrazine is heated under reflux and a nitrogen atmosphere for one hour, evaporated in vacuo, and coevaporated with xylenes. The residue is distributed between a mixture of ethyl acetate and water. The aqueous layer is reextracted with ethyl acetate and the dried ethyl acetate solution is evaporated in vacuo to provide 9.0 g of crude product. Purification of this material by silica gel chromatography (ethyl acetate) provides pure 4-hydrazino-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. customthe dried ethyl acetate solution is evaporated in vacuo
  6. customto provide 9.0 g of crude product
  7. customPurification of this material by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-2bd2a50ff3894e29b6900764fd9a85fa
Source dataset
uspto-grants-1984_03
Patent number
US04439604

Reaction notes

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