Hydrochloric Acid → 6-Amino-2-butoxy-9-(3-pyrrolidin-1-ylpropyl)-7,9-dihydro-8H-purin-8-one

HRID 590494Notes

Reaction equation

HRID 590494 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:23]C)[N:12]2[CH2:15][CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:8]([NH2:25])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O1CCOCC1>CO>[NH2:25][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:23])[N:12]2[CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 592525952-(Butyloxy)-8-(methyloxy)-9-[3-(1-pyrrolidinyl)propyl]-9H-purin-6-amine

Product 1

HCID 250720776-Amino-2-butoxy-9-(3-pyrrolidin-1-ylpropyl)-7,9-dihydro-8H-purin-8-oneYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(Butyloxy)-8-(methyloxy)-9-[3-(1-pyrrolidinyl)propyl]-9H-purin-6-amine (49 mg, 0.141 mmol) was dissolved in methanol (5 ml) and 4M hydrogen chloride in 1,4-dioxane (0.879 ml, 3.52 mmol) was added and the mixture stirred at room temperature for 5 hours. The solvent was removed in vacuo to give a cream solid which was dissolved in methanol and loaded onto an aminopropyl SPE cartridge (2 g) and eluted with methanol. The solvent was evaporated to give the title compound as a white solid (43 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a cream solid which
  3. washeluted with methanol
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-78eaa910c6004d269fcccc905ff02b4c
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

Loading…