Sodium borohydride → 9-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine

HRID 1646668Notes

Reaction equation

[N:1]([C:4]1[N:12]=[C:11]([F:13])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:14]1[O:34][C@H:33]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:15]1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N+]=[N-].[BH4-].[Na+]>CC(O)C.O>[CH2:17]([O:16][C@H:15]1[C@H:24]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:33]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:34][C@H:14]1[N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:11]([F:13])=[N:12][C:4]=2[NH2:1])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 25 °C

Procedure

6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine (0.28 g, 0.48 Mmol) was dissolved in warm 2-propanol (3 mL) and then cooled to about 25° C. To the resulting solution was added sodium borohydride (18 mg, 0.48 Mmol) and the mixture was stirred at room temperature for 10 minutes and then at reflux for 15 minutes. The reaction was complete as determined by TLC so it was cooled to room temperature and diluted with water (10 mL). The resulting precipitate was recovered by filtration to obtain 0.19 g of the title compound; mp 159°-161° C. (from toluene/ethanol). This material was identical by IR and TLC with an authentic sample of the title compound.

Workup

temperatureat reflux for 15 minutes
temperaturewas cooled to room temperature
filtrationThe resulting precipitate was recovered by filtration

Sources & evidence

ORD record: ord-872fe6b8bbe64a5a8d97692cf5f636aa
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180824

Reaction notes

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