2-Methyl-1-butanol → HCID 57699796, compound

HRID 1010961Notes

Reaction equation

HRID 1010961 reaction equation
[CH3:1][CH:2]([CH2:5][CH3:6])[CH2:3][OH:4].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>COCCOC.O>[CH3:1][CH:2]([CH2:5][CH3:6])[CH2:3][O:4][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

Participants

6

Reactant 3

HCID 87232-Methyl-1-butanolHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23676156Sodium t-butoxide

Product 1

HCID 57699796HCID 57699796, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To 2-methyl-1-butanol (0.855 mL) in DME (4 mL) was added sodium tert-butoxide (760 mg). 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 followed by DME (4 mL). The reaction was heated at 110° C. overnight. The mixture was cooled and concentrated in vacuo to give a yellow residue. The residue was taken up in water (30 mL) and extracted with EtOAc (2×30 mL). The organics were separated and washed with brine (30 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a yellow/brown residue. This material was taken on to the next step without further purification.

Workup

  1. temperatureThe reaction was heated at 110° C. overnight
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customto give a yellow residue
  5. extractionextracted with EtOAc (2×30 mL)
  6. customThe organics were separated
  7. washwashed with brine (30 mL)
  8. customThe organics were separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbc04edd0c944c299a484eef79ab2974
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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