Sodium Iodide → HCID 53355168, compound

HRID 2038190Notes

Reaction equation

HRID 2038190 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21]C)[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Cl)=[C:8]([NH2:23])[N:7]=1)[CH2:2][CH2:3][CH3:4].CC#N.[N:27]1([CH2:33][CH2:34][OH:35])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(C(C)C)C(C)C.[I-].[Na+]>Cl.CO>[NH2:23][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:21])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:30]1[CH2:31][CH2:32][N:27]([CH2:33][CH2:34][OH:35])[CH2:28][CH2:29]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 76771-(2-Hydroxyethyl)piperazineHCID 81531DiisopropylethylamineHCID 592526362-(Butyloxy)-9-(5-chloropentyl)-8-(methyloxy)-9H-purin-6-amine2×

Product 1

HCID 53355168HCID 53355168, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Conditions

Temperature
60 °C

Procedure

An aliquot (0.2 mL, 0.1 mmol) of a solution of 2-(butyloxy)-9-(5-chloropentyl)-8-(methyloxy)-9H-purin-6-amine (for example, as prepared for Intermediate 44) in MeCN (prepared by dissolving 410 mg, 1.2 mmol in MeCN (2.4 mL)) was added to 2-(1-piperazinyl)ethanol (commercially available, for example, from Aldrich) (0.1 mmol) in a test tube. DIPEA (50 μl, 3 equivalents) and sodium iodide (5 mg) were added. The reaction mixture was heated to 60° C. for 18 hours in a Radleys greenhouse. The samples were filtered then DMSO (0.3 mL) was added and the solution and purified MDAP on Xbridge column using Acetonitrile Water with an ammonium carbonate modifier. The solvent was evaporated in vacuo using the Genevac to give an intermediate. 2N HCl/MeOH (200 μL) added to each vial, capped and stood at room temperature for 4 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The residue was redissolved in methanol (0.5 mL) and applied to top of an aminopropyl SPE (0.1 g, 3 mL, preconditioned in methanol (1.5 mL)). The cartridge was washed methanol (2×1.5 mL). The solvent was removed to give the title compound (0.0175 g).

Workup

  1. filtrationThe samples were filtered
  2. additionDMSO (0.3 mL) was added
  3. customthe solution and purified MDAP on Xbridge column
  4. customThe solvent was evaporated in vacuo
  5. customto give an intermediate
  6. customcapped
  7. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  8. dissolutionThe residue was redissolved in methanol (0.5 mL)
  9. washThe cartridge was washed methanol (2×1.5 mL)
  10. customThe solvent was removed

Sources & evidence

ORD record
ord-f6c6da8792e2460ba6974371b921db7a
Source dataset
uspto-grants-2013_11
Patent number
US08575340B2

Reaction notes

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