Dimethyl Sulfoxide → 6-Amino-2-(butyloxy)-9-{[1-(1-methylethyl)-3-piperidinyl]methyl}-7,9-dihydro-8H-purin-8-one

HRID 2403899Notes

Reaction equation

HRID 2403899 reaction equation
I[CH:2]([CH3:4])[CH3:3].[CH2:5]([O:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[C:15]([O:26]C)[N:16]2[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]2)=[C:12]([NH2:28])[N:11]=1)[CH2:6][CH2:7][CH3:8].CCN(C(C)C)C(C)C.CS(C)=O>CN(C=O)C>[NH2:28][C:12]1[N:11]=[C:10]([O:9][CH2:5][CH2:6][CH2:7][CH3:8])[N:18]=[C:17]2[C:13]=1[NH:14][C:15](=[O:26])[N:16]2[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH:2]([CH3:4])[CH3:3])[CH2:21]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6362Isopropyl iodideHCID 81531DiisopropylethylamineHCID 583062412-butoxy-8-methoxy 9-(piperidin-3-ylmethyl)-9H-purin-6-amine

Product 1

HCID 672345386-Amino-2-(butyloxy)-9-{[1-(1-methylethyl)-3-piperidinyl]methyl}-7,9-dihydro-8H-purin-8-oneYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Iodopropane (0.1 mmol) was weighed into a vial and an aliquot (0.3 ml, 0.1 mmol) of a solution of 2-(butyloxy)-8-(methyloxy)-9-(3-piperidinylmethyl)-9H-purin-6-amine (802 mg, 2.398 mmol) suspended in DMF (7.2 ml) was added. DIPEA (40 μl, 0.229 mmol) was added and the tube was capped and shaken to aid dispersion then allowed to stand at room temperature (18 hours). DMSO (400 uL) was added and the mixture purified by Mass Directed AutoPrep (Method A). The solvent was evaporated in vacuo using the Genevac. The residue was redissolved in 4M HCl/dioxane (0.5 ml), capped and stood at room temperature for 18 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The material was redissolved in methanol (0.5 ml), and applied to a 0.5 g aminopropyl SPE (preconditioned with methanol, 2 CV). The cartridge was eluted with methanol (2 ml), the solvent was removed to give the title compound (11.1 mg).

Workup

  1. additionwas added
  2. customthe tube was capped
  3. customto stand at room temperature
  4. custom(18 hours)
  5. customthe mixture purified by Mass Directed AutoPrep (Method A)
  6. customThe solvent was evaporated in vacuo
  7. dissolutionThe residue was redissolved in 4M HCl/dioxane (0.5 ml)
  8. customcapped
  9. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  10. dissolutionThe material was redissolved in methanol (0.5 ml)
  11. washThe cartridge was eluted with methanol (2 ml)
  12. customthe solvent was removed

Sources & evidence

ORD record
ord-57eeacfea0f44cfeace7341a9338b4dc
Source dataset
uspto-grants-2014_08
Patent number
US08802684B2

Reaction notes

Loading…