Tributylphosphine → HCID 58306069, compound

HRID 1044858Notes

Reaction equation

HRID 1044858 reaction equation
[CH2:1]([O:5][C:6]1[NH:7][C:8]([NH2:17])=[C:9]2[C:13]([N:14]=1)=[N:12][C:11]([O:15][CH3:16])=[N:10]2)[CH2:2][CH2:3][CH3:4].[CH2:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26]O)[CH2:22][CH2:21]1)[CH3:19].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]2[CH2:26][CH:23]2[CH2:24][CH2:25][N:20]([CH2:18][CH3:19])[CH2:21][CH2:22]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 15512642(1-Ethyl-4-piperidinyl)methanolHCID 178450356HCID 178450356, compound

Product 1

HCID 58306069HCID 58306069, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine (300 mg, 1.264 mmol), (1-ethyl-4-piperidinyl)methanol (362 mg, 2.53 mmol) and tributylphosphine (0.624 ml, 2.53 mmol) were dissolved in THF (12 ml). 1,1′-(Azodicarbonyl)dipiperidine (638 mg, 2.53 mmol) was added and the reaction mixture stirred at rt overnight. The solvent was removed in vacuo and the residue purified by column chromatography, loading in dichloromethane and purified on Flashmaster II silica (Si) 20 g using a 0-100% ethyl acetate in cyclohexane+0-20% methanol (+1% Et3N) gradient over 30 mins. The appropriate fractions were combined and evaporated in vacuo. The material (300 mg) was dissolved in 1:1 MeOH:DMSO 3 ml and re-purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound as a clear gum (60 mg). LCMS (System A): tRET=0.57 min; MH+ 363

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by column chromatography, loading in dichloromethane
  3. custompurified on Flashmaster II silica (Si) 20 g
  4. customover 30 mins
  5. customevaporated in vacuo
  6. dissolutionThe material (300 mg) was dissolved in 1:1 MeOH
  7. customDMSO 3 ml and re-purified by Mass Directed AutoPrep (Method A)
  8. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-fccff12b8fd3428a96b0e54de79fbb8f
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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