Ammonia → HCID 14842880, compound

HRID 966389Notes

Reaction equation

HRID 966389 reaction equation
[H][H].[NH3:3].[CH2:4]([O:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[CH:17][N:18]2[C@@H:21]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@@H:27]([O:28]C(=O)C)[C@H:22]2[O:23]C(=O)C)=[C:14](Cl)[N:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[CH2:4]([O:11][C:12]1[N:13]=[C:14]([NH2:3])[C:15]2[N:16]=[CH:17][N:18]([C:19]=2[N:20]=1)[C@@H:21]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:27]([OH:28])[C@H:22]1[OH:23])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 59107260HCID 59107260, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14842880HCID 14842880, compoundYield 70%

Procedure

A compound having a structure of the above formula was prepared where the substituents R1 and R2 are hydrogen and R3 is benzyl (—CH2C6H5). The compound (C17H19N5O5) was prepared by reaction of ammonia with 2-benzyloxy-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 3) as described in Example 2, Step E. The final product was isolated in 70% yield as a solid with melting point of 178-179 ° C. 1H-NMR (DMSO-d6): δ 3.49 (m, 1H); 3.61 (m, 1H); 3.9 (m, 1H); 4.12 (m, 1H); 4.58 (m, 1H); 5.18 (d, 2H, J=4); 5.3 (s, 2H); 5.42 (d, 1H, J=6); 5.79 (d, 1H, J=6); 7.37 (m, 7H); 8.16 (s, 1H).

Workup

  1. customwas prepared where the substituents

Sources & evidence

ORD record
ord-52db01191be245a18f13953c67ee6415
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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