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

HRID 1010967Notes

Reaction equation

HRID 1010967 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH2:17])[N:3]=1.[CH3:18][CH:19]([OH:23])[CH2:20][CH2:21][CH3:22].[H-].[Na+]>>[CH3:18][CH:19]([O:23][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH2:17])[N:3]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 223862-PentanolHCID 24758Sodium hydrideHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenine

Product 1

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

Conditions

Temperature
50 °C

Procedure

In a separate flask, a suspension of 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (500 mg) and 2-pentanol (3.8 mL) was heated to 50° C. Sodium hydride (396 mg, 60% dispersion) was added in portions and the reaction was stirred at 50° C. for 72 h. The reaction was cooled and quenched with water (10 mL) and was extracted with EtOAc (3×25 mL). The combined organics were washed with brine (30 mL), dried over MgSO4, filtered and concentrated in vacuo to give crude title compound as a yellow oil.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with water (10 mL)
  3. extractionwas extracted with EtOAc (3×25 mL)
  4. washThe combined organics were washed with brine (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ef20d786e8b46bb91d163cb8d28feba
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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