Sulfuric Acid → HCID 21882936, compound

HRID 722099Notes

Reaction equation

HRID 722099 reaction equation
[Br:1][C:2]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[C:17]([O:24][CH3:25])=[CH:16][C:3]=1[CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([NH2:15])=[N:9][C:10]=2[Cl:14].OS(O)(=O)=O.[C:31](OC(=O)C)(=[O:33])[CH3:32]>>[Br:1][C:2]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[C:17]([O:24][CH3:25])=[CH:16][C:3]=1[CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([NH:15][C:31](=[O:33])[CH3:32])=[N:9][C:10]=2[Cl:14]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 11396254HCID 11396254, compound

Product 1

HCID 21882936HCID 21882936, compound

Procedure

A suspension of 9-(2-bromo-3,4,5-trimethoxy-benzyl)-6-chloro-9H-purin-2-ylamine (example 51) in acetic anhydride was treated with a catalytic amount of conc. H2SO4 at r.t. for 3 h. Work-up and purification by preparative TLC (EtOAc:hexane 9:1) gave the title compound. HPLC Rt: 5.603 min. 1H-NMR (CDCl3): δ 8.20 (s, 1H), 8.10 (s, 1H), 7.00 (s, 1H), 5.47 (s, 2H), 3.92 (s, 3H), 3.90 (s, 3H), 3.86 (s, 3H), 2.51 (s, 3H).

Workup

  1. custompurification by preparative TLC (EtOAc:hexane 9:1)

Sources & evidence

ORD record
ord-d5132588a35743299f7a521b1dd419a8
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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