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Potassium Carbonate → 6-Amino-2-(butyloxy)-9-[(1-cyclohexyl-4-piperidinyl)methyl]-7,9-dihydro-8H-purin-8-one

HRID 2403932
Notes
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Reaction equation

HRID 2403932 reaction equation
I[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:29]C)[N:19]2[CH2:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[C:15]([NH2:31])[N:14]=1)[CH2:9][CH2:10][CH3:11].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CS(C)=O>[NH2:31][C:15]1[N:14]=[C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:21]=[C:20]2[C:16]=1[NH:17][C:18](=[O:29])[N:19]2[CH2:22][CH:23]1[CH2:24][CH2:25][N:26]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:27][CH2:28]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12289Iodocyclohexane2×HCID 81531Diisopropylethylamine2×HCID 583062032-(Butyloxy)-8-(methyloxy)-9-(4-piperidinylmethyl)-9H-purin-6-amine

Product 1

HCID 672345686-Amino-2-(butyloxy)-9-[(1-cyclohexyl-4-piperidinyl)methyl]-7,9-dihydro-8H-purin-8-oneYield 4.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Iodocyclohexane (0.1 mmol) was weighed into a tube and an aliquot (0.4 ml, 0.12 mmol) of a solution of 2-(butyloxy)-8-(methyloxy)-9-(4-piperidinylmethyl)-9H-purin-6-amine (0.402 g mg, 1.2 mmol) suspended in DMF (4.8 ml) was added to each tube. DIPEA (40 μl, 0.229 mmol) and potassium carbonate (46 mg) was added to each tube, the tube was heated at 50° C. for 18 hours. An additional portion of iodocyclohexane (15 μl) and DIPEA (40 μl) was added and heating continued for a further 18 hours. DMSO (250 uL) was added and the solution 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 (0.2 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 sample was dissolved in 1:1 DMSO:MeOH and purified by MDAP (Method C) and the solvent was evaporated in vacuo using the Genevac. The material was redissolved in methanol (0.5 ml), and applied to top of 0.1 g aminopropyl SPE (preconditioned with methanol, 1.5 ml). The cartridge was eluted with methanol (1.5 ml), the solvent was removed to give the title compound (1.9 mg).

Workup

  1. additionwas added to each tube
  2. temperatureheating
  3. customthe solution and the mixture purified by Mass Directed AutoPrep (Method A)
  4. customThe solvent was evaporated in vacuo
  5. dissolutionThe residue was redissolved in 4M HCl/dioxane (0.2 ml)
  6. customcapped
  7. waitstood at room temperature for 18 hours
  8. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  9. dissolutionThe sample was dissolved in 1:1 DMSO
  10. customMeOH and purified by MDAP (Method C)
  11. customthe solvent was evaporated in vacuo
  12. dissolutionThe material was redissolved in methanol (0.5 ml)
  13. washThe cartridge was eluted with methanol (1.5 ml)
  14. customthe solvent was removed

Sources & evidence

ORD record
ord-f4ec00709d594e32bd0d20bc8616f68d
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08802684B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes