Ammonia → 7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1904108Notes

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.[NH3:41]>CO>[CH2:14]([O:13][C@H:12]1[C@H:21]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:30]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:31][C@H:11]1[N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:41])[C:3]=2[CH:10]=[CH:9]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3 g of 4-chloro-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine, 3 ml of methanol, and 20 ml of liquid ammonia is placed in a stainless steel reactor and heated at 100° C. for 5 hours. The ammonia is allowed to evaporate and the residue, after evaporation of the methanol, is distributed between ethyl acetate and water. The aqueous layer is reextracted with ethyl acetate and the dried (MgSO4) ethyl acetate solution is evaporated in vacuo to provide 2.6 g of 7-(2,3,5tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine as a crude yellow syrup. Chromatography of this material over silica gel with ethyl acetate provides 2.6 g of pure product as a colorless syrup.

Workup

customis placed in a stainless steel reactor
customto evaporate
customthe residue, after evaporation of the methanol
dry with materialthe dried (MgSO4) ethyl acetate solution
customis evaporated in vacuo

Sources & evidence

ORD record: ord-e5cdd3210e55405a8a5db0b553f61fd6
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04439604

Reaction notes

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