Ethylamine → HCID 59107263, compound

HRID 966391Notes

Reaction equation

[H][H].[CH2:3]([NH2:5])[CH3:4].Cl[C:7]1[N:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][N:11]2[C@@H:27]1[O:39][C@H:38]([CH2:40][O:41]C(=O)C)[C@@H:33]([O:34]C(=O)C)[C@H:28]1[O:29]C(=O)C>>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][O:16][C:14]2[N:15]=[C:7]([NH:5][CH2:3][CH3:4])[C:8]3[N:9]=[CH:10][N:11]([C:12]=3[N:13]=2)[C@@H:27]2[O:39][C@H:38]([CH2:40][OH:41])[C@@H:33]([OH:34])[C@H:28]2[OH:29])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

Reactant 3

HCID 6341Ethylamine

HCID 59107259HCID 59107259, compound

HCID 178418361HCID 178418361, compound

Product 1

HCID 59107263HCID 59107263, compoundYield 60%

Procedure

A compound having a structure of the above formula was prepared where the substituent R1 is —CH2CH3, R2 is hydrogen, and R3 is 4-nitrobenzyl (—CH2(4-nitro)C6H4). The compound (C19H22N6O7) was prepared by reaction of ethylamine 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 60% yield as a solid with a melting point of 210-213° C. 1H-NMR (DMSO-d6): δ 1.05 (1, 3H, J=8); 3.4 (m, 2H); 3.5 (m, 1H); 3.6 (m, 1H); 3.85 (m, 1H); 4.05 (m, 1H); 4.6 (m, 1H); 5.2 (m, 2H); 5.4 (d, 1H, J=6); 5.45 (s, 2H); 5.8 (d, 1H, J=6); 7.8 (d, 2H, J=8); 8 (bt, 1H); 8.2 (s, 1H); 8.25 (d, 2H, J=8).

Workup

customwas prepared where the substituent R1

Sources & evidence

ORD record: ord-759cf06e5cf540b1a6c3fc90f3ee66a4
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951932B2

Reaction notes

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