Ammonia → HCID 59107261, compound

HRID 966392Notes

Reaction equation

HRID 966392 reaction equation
[H][H].[NH3:3].Cl[C:5]1[N:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@@H:25]1[O:37][C@H:36]([CH2:38][O:39]C(=O)C)[C@@H:31]([O:32]C(=O)C)[C@H:26]1[O:27]C(=O)C>>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:12]2[N:13]=[C:5]([NH2:3])[C:6]3[N:7]=[CH:8][N:9]([C:10]=3[N:11]=2)[C@@H:25]2[O:37][C@H:36]([CH2:38][OH:39])[C@@H:31]([OH:32])[C@H:26]2[OH:27])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 59107259HCID 59107259, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59107261HCID 59107261, compoundYield 80%

Procedure

A compound having a structure of the above formula was prepared where the substituents R1 and R2 are hydrogen and R3 is 4-nitrobenzyl (—CH2(4-nitro)C6H4). The compound (C17H18N6O7) was prepared by reaction of ammonia with 6-chloro-2-(4-nitrobenzyl)oxy-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 4) as described in Example 2, Step E. The final product was isolated in 80% yield as a solid with a melting point of 174-176° C. 1H-NMR (DMSO-d6): δ 3.5 (m, 1H); 3.6 (m, 1H); 3.8 (d, 1H, J=4); 4.1 (m, 1H); 4.56 (m, 1H); 5.16 (m, 2H); 5.4 (d, 1H, J=6); 5.47 (s, 2H); 5.77 (d, 1H, J=6); 7.43 (bs, 2H); 7.7 (d, 2H, J=8); 8.18 (s, 1H); 8.24 (d, 2H, J=8).

Workup

  1. customwas prepared where the substituents

Sources & evidence

ORD record
ord-b7ef49f00e0a48a7af98bd2d7ea9223f
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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