Ammonia → HCID 90402696, compound

HRID 2200665Notes

Reaction equation

HRID 2200665 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:12]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=3)=[N:11][C:10]=2[N:9]([CH3:37])[C:8]1=[O:38].[NH3:39]>CO>[NH2:39][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:12]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=3)=[N:11][C:10]=2[N:9]([CH3:37])[C:8]1=[O:38]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90403350HCID 90403350, compound

Product 1

HCID 90402696HCID 90402696, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-(2-bromoethoxy)ethyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (100 mg, 0.16 mmol) was dissolved in a preformed solution of ammonia in methanol (15 mL). The reaction was heated at 60° C. overnight in a sealed tube. The reaction was cooled to room temperature and the solvent was evaporated. The residue was purified by preparative HPLC to give 1-(2-(2-aminoethoxy)ethyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (35 mg, 39% yield) as white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent was evaporated
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ff64341b89fe4d5c8a89aabc296827c3
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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