N-Iodosuccinimide → 6-Chloro-7-iodo-7-deazapurine

HRID 915873Notes

Reaction equation

HRID 915873 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.[I:11]N1C(=O)CCC1=O>C1COCC1>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178418725HCID 178418725, compound2×

Product 1

HCID 148092816-Chloro-7-iodo-7-deazapurine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The tricyclic nucleoside 6.7 was synthesized starting from 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 2.1. The nucleobase 2.1 was treated with N-iodosuccinimide in THF at room temperature for 4 hr to provide 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 6.1. Then 6.1 was converted to the corresponding sodium salt with sodium hydride in acetonitrile and reacted with bromo-sugar 2.4 ((i)Helv. Chim. Acta. 1995, 78, 486; (ii) WO 02/057287, 2002), to give nucleoside 6.2. which was directly converted to 4-amino-5-iodo-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 6.3. A Stille coupling reaction between nucleoside 6.3 and Z-3-tributylstannylacrylate provided compound 6.4. The cyclization of compound 6.4 was accomplished by heating in DBU/dioxane overnight to afford the protected tricyclic nucleoside 6.5, which was then treated with boron trichloride in CH2Cl2 to produce nucleoside 6.6.

Sources & evidence

ORD record
ord-28ca1e4004ad45e6b179c59bc3f10bda
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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