Nitric Acid → HCID 21883012, compound

HRID 722097Notes

Reaction equation

HRID 722097 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1.[N+]([O-])(O)=O.[CH3:29][CH2:30][O:31]C(C)=O.CCCCCC>C(O)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]([NH:11][C:30](=[O:31])[CH3:29])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 16735062HCID 16735062, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 21883012HCID 21883012, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-chloro-9-(3,4,5-trimethoxy-benzyl)-9H-purin-2-ylamine in acetic acid was treated with fuming HNO3 at 0° C. for 15 min. Work-up and preparative TLC (EtOAc:hexane 1:1) gave N-[6-chloro-9-(3,4,5-trimethoxy-benzyl)-9H-purin-2-yl]-acetamide. HPLC Rt: 5.744 min. 1H-NMR (CDCl3): δ 8.09 (s, 1H), 6.58 (s, 2H), 5.33 (s, 2H), 3.85 (s, 3H), 3.85 (s, 6H), 2.43 (s, 3H).

Sources & evidence

ORD record
ord-459a2574dff045229660b18df9171d61
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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