2-Pentanol → 2-[(1-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1010966Notes

Reaction equation

HRID 1010966 reaction equation
[CH3:1][CH:2]([OH:6])[CH2:3][CH2:4][CH3:5].CC(C)([O-])C.[Na+].Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1>>[CH3:1][CH:2]([O:6][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 223862-PentanolHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23676156Sodium t-butoxide

Product 1

HCID 576995892-[(1-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Procedure

To 2-pentanol (3.65 mL) was added sodium tert-butoxide (760 mg) in portions over 5 mins. The mixture was stirred at room temperature until homogeneous. 2-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (500 mg) was added and the reaction was heated at 50° C. overnight, then for a further 72 h. The reaction mixture was cooled and quenched with water (10 mL) and was extracted with EtOAc (3×25 mL). The organics were combined, washed with brine (30 mL), dried over MgSO4, filtered and concentrated in vacuo to give crude title compound as a viscous yellow oil.

Workup

  1. temperaturethe reaction was heated at 50° C. overnight
  2. temperatureThe reaction mixture was cooled
  3. customquenched with water (10 mL)
  4. extractionwas extracted with EtOAc (3×25 mL)
  5. washwashed with brine (30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf585b508a12478bb8564f00fc3c87d9
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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