Ammonia → HCID 59107258, compound

HRID 966395Notes

Reaction equation

HRID 966395 reaction equation
[H][H].[NH3:3].Cl[C:5]1[N:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[C@@H:26]1[O:38][C@H:37]([CH2:39][O:40]C(=O)C)[C@@H:32]([O:33]C(=O)C)[C@H:27]1[O:28]C(=O)C>>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][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:26]2[O:38][C@H:37]([CH2:39][OH:40])[C@@H:32]([OH:33])[C@H:27]2[OH:28])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 59107262HCID 59107262, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59107258HCID 59107258, compoundYield 10%

Procedure

A compound having a structure of the above formula was prepared where the substituents R1 and R2 are hydrogen and R3 is —CH2CH2CH2(3-OCH3)C6H4. The compound (C20H25N5O6) was prepared by reaction of ammonia with 6-chloro-2-[3-(3-methoxyphenyl)propyloxy]-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 7) as described in Example 2, Step E. The final product was isolated in 10% yield as a solid with a melting point of 85-87° C. 1H-NMR (DMSO-d6): 1.97 (t, 2H, J=6); 2.69 (t, 2H, J=6); 3.54 (m, 2H); 3.71 (s, 3H); 3.95 (m, 1H); 4.15 (m, 3H); 4.58 (m, 1H); 5.19 (m, 2H); 5.42 (d, 1H, J=6); 5.77 (d, 1H, J=6); 6.77 (m, 3H); 7.19 (t, 1H, 8); 7.3 (bs, 2H); 8.14 (s, 1H).

Workup

  1. customwas prepared where the substituents

Sources & evidence

ORD record
ord-fbd6e65fef214515ade3b2c015c462f4
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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