Ethylamine → 2-(Benzyloxy)-N-ethyladenosine

HRID 966390Notes

Reaction equation

HRID 966390 reaction equation
[H][H].[CH2:3]([NH2:5])[CH3:4].[CH2:6]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[C@@H:23]2[O:35][C@H:34]([CH2:36][O:37]C(=O)C)[C@@H:29]([O:30]C(=O)C)[C@H:24]2[O:25]C(=O)C)=[C:16](Cl)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:6]([O:13][C:14]1[N:15]=[C:16]([NH:5][CH2:3][CH3:4])[C:17]2[N:18]=[CH:19][N:20]([C:21]=2[N:22]=1)[C@@H:23]1[O:35][C@H:34]([CH2:36][OH:37])[C@@H:29]([OH:30])[C@H:24]1[OH:25])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 59107260HCID 59107260, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 591072552-(Benzyloxy)-N-ethyladenosineYield 40%

Procedure

A compound having a structure of the above formula was prepared where the substituent R1 is —CH2CH3, R2 is hydrogen, and R3 is benzyl (—CH2C6H5). The compound (C19H23N5O5) was prepared by reaction of ethylamine 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 40% yield as a solid with melting point of 170-171° C. 1H-NMR (DMSO-d6): δ 1.13 (t, 3H, J=8); 3.6 (m, 4H); 3.9 (m, 1H); 4.1 (m, 1H); 4.5 (m, 1H); 5.18 (m, 2H); 5.32 (s, 2H); 5.42 (d, 1H, J×6); 5.78 (d, 1H, J=6); 7.41 (m, 5H); 7.93 (bm, 1H); 8.15 (s, 1H).

Workup

  1. customwas prepared where the substituent R1

Sources & evidence

ORD record
ord-b9a31fe0fef34ecf9c1c131d437dde49
Source dataset
uspto-grants-2005_10
Patent number
US06951932B2

Reaction notes

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