Hydrochloric Acid → 6-Amino-2-(butyloxy)-9-[3-(2-piperidinyl)propyl]-7,9-dihydro-8H-purin-8-one

HRID 1044950Notes

Reaction equation

HRID 1044950 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:24]C)[N:12]2[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]2)=[C:8]([NH2:26])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O1CCOCC1>CO.CS(C)=O>[NH2:26][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:24])[N:12]2[CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 583061842-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amine

Product 1

HCID 672338476-Amino-2-(butyloxy)-9-[3-(2-piperidinyl)propyl]-7,9-dihydro-8H-purin-8-oneYield 76.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

2-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amine (41.89 mg, 0.116 mmol) in methanol (3 ml) was treated with 4 molar HCl solution in 1,4-dioxane (0.722 mL, 2.89 mmol) and stirred at ambient temperature in a capped vial overnight. The clear reaction solution was blown down under N2 and then dissolved in 1 ml 1:1 DMSO:MeOH and purified by MDAP (Method A). The appropriate fraction was evaporated under N2 in a Radleys blow down unit to afford the title compound as a white solid (31.1 mg).

Workup

  1. customMeOH and purified by MDAP (Method A)
  2. customThe appropriate fraction was evaporated under N2 in a Radleys blow down unit

Sources & evidence

ORD record
ord-399a8263032c4bdfb404997beb883dc9
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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