Ammonia → HCID 10806990, compound

HRID 966393Notes

Reaction equation

HRID 966393 reaction equation
[H][H].[NH3:3].[CH2:4]([O:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@@H:18]2[O:30][C@H:29]([CH2:31][O:32]C(=O)C)[C@@H:24]([O:25]C(=O)C)[C@H:19]2[O:20]C(=O)C)=[C:11](Cl)[N:10]=1)[CH2:5][CH2:6][CH3:7]>>[CH2:4]([O:8][C:9]1[N:10]=[C:11]([NH2:3])[C:12]2[N:13]=[CH:14][N:15]([C:16]=2[N:17]=1)[C@@H:18]1[O:30][C@H:29]([CH2:31][OH:32])[C@@H:24]([OH:25])[C@H:19]1[OH:20])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 59107266HCID 59107266, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10806990HCID 10806990, compoundYield 30%

Procedure

A compound having a structure of the above formula was prepared where the substituents R1 and R2 are hydrogen and R3 is n-butyl (—CH2CH2CH2CH3). The compound (C14H21N5O5) was prepared by reaction of ammonia with 2-butyloxy-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 5) as described in Example 2, Step E. The final product was isolated in 30% yield as a solid with a melting point of 145-146° C. 1H-NMR (DMSO-d6): δ 0.9 (t, 3H); 1.37 (m, 2H, J=8); 1.65 (m, 2H, J=8); 3.66 (m, 2H); 3.97 (m, 1H); 4.18 (m, 3H); 4.57 (m, 1H), 4.95 (d, 1H, J=6); 5.23 (m, 2H); 5.78 (d, 1H, J=6); 6.9 (bs, 2H); 7.94 (s, 1H).

Workup

  1. customwas prepared where the substituents

Sources & evidence

ORD record
ord-49b7606844ed418bb7f9320c0880547d
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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