HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1904110Generated: October 25, 2026
Sodium hydride → 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
https://huagongshe.com/reaction/1904110
Participants
| Role | Name | HCID | Charge |
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| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine | HCID 5324414 | — |
| Reactant | (2R,3R,4S,5R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-chlorotetrahydrofuran | HCID 10895454 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | HCID 13277177 | — |
Reaction Steps
A suspension of 3.1 g sodium hydride, 25.9 g of 4-chloro-2-methylmercapto-7H-pyrrolo[2,3-d]pyrimidine, and 250 ml of dry dimethylformamide (DMF) is stirred at 50° C. for 0.5 hour, cooled, and added to 62.8 g of 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride. The solution is stirred at ambient temperature for 15 hours, concentrated in vacuo, and distributed between a mixture of ethyl acetate and water. Chromatography of the dried (MgSO4) layer over silica gel with 4:1 toluene-ethyl acetate provides 76 g of yellow, syrupy 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04439604 |
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| Source dataset | uspto-grants-1984_03 |
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| ORD ID | ord-f2a5eca74f644fa99da0b3eeff497609 |
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| Source note | uspto-grants-1984_03 |
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