2-Chloro-9-[2-deoxy-3,5-di-o-(p-toluoyl)-beta-d-erythro-pentofuranosyl]-6-(2-isopropylimidazol-1-yl)purine → Purine

HRID 2264862Notes

Reaction equation

HRID 2264862 reaction equation
C1(C2N=CN([C:18]3[N:26]=[CH:25][N:24]=[C:23]4[C:19]=3[NH:20][CH:21]=[N:22]4)C=2C2C=CC=CC=2)C=CC=CC=1.ClC1N=C2C(N=CN2[C@@H]2O[C@H](COC(C3C=CC(C)=CC=3)=O)[C@@H](OC(C3C=CC(C)=CC=3)=O)C2)=C(N2C=CN=C2C(C)C)N=1>>[N:26]1[CH:18]=[C:19]2[C:23]([N:22]=[CH:21][NH:20]2)=[N:24][CH:25]=1

Participants

3

Reactant 2

HCID 160892082-Chloro-9-[2-deoxy-3,5-di-o-(p-toluoyl)-beta-d-erythro-pentofuranosyl]-6-(2-isopropylimidazol-1-yl)purineHCID 131728593HCID 131728593, compound

Product 1

HCID 1044Purine

Procedure

Benzylation of sterically hindered 6-(imidazol-1-yl)purines can result in mixtures of benzylated and nonbenzylated products such as when benzylating 2-chloro-9-[2-deoxy-3,5-di-O-p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(4,5-diphenylimidazol-1-yl)purine, 2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-isopropylimidazol-1-yl)purine. Partial decomposition can also result with 6-(2-benzylimidazol-1-yl)-2-chloro-9-[2-deoxy-3,5-di-O-p-toluoyl)-β-D-erythro-pentofuranosyl]purine.

Sources & evidence

ORD record
ord-681278adaf014201a22551b3206ca90d
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

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