Ammonia → HCID 16735064, compound

HRID 722103Notes

Reaction equation

HRID 722103 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]=2Cl.[NH3:26]>CO>[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[NH2:26]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11396254HCID 11396254, compound

Product 1

HCID 16735064HCID 16735064, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 9-(2-bromo-3,4,5-trimethoxy-benzyl)-6-chloro-9H-purin-2-ylamine (see example 51) in MeOH was treated with NH3 (7N in MeOH) in a pressure vessel at 90° C. for 16 h. Work-up and purification by preparative TLC (EtOAc:hexane 3:1) gave the title compound. HPLC Rt: 4.884 min. 1H-NMR (DMSO-d6): δ 7.67 (s, 1H), 6.71 (s, 2H), 6.60 (s, 1H), 5.84 (s, 2H), 5.17 (s, 2H), 3.80 (s, 3H), 3.76 (s, 3H), 3.66 (s, 3H).

Workup

  1. custompurification by preparative TLC (EtOAc:hexane 3:1)

Sources & evidence

ORD record
ord-3907764347874fd98f4a42cb2155ce3c
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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