Methanol → 2-([2-[(1-Methylethyl)oxy]ethyl}oxy)-8-(methoxy)-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine

HRID 1011048Notes

Reaction equation

HRID 1011048 reaction equation
[Na].Br[C:3]1[N:4]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[C:5]2[C:10]([N:11]=1)=[C:9]([NH2:12])[N:8]=[C:7]([O:13][CH2:14][CH2:15][O:16][CH:17]([CH3:19])[CH3:18])[N:6]=2.[CH3:26][OH:27]>>[CH3:18][CH:17]([O:16][CH2:15][CH2:14][O:13][C:7]1[N:6]=[C:5]2[C:10]([N:11]=[C:3]([O:27][CH3:26])[N:4]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:9]([NH2:12])[N:8]=1)[CH3:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 576995988-bromo-2-({2-[(1-methylethyl)oxy]ethyl}oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996792-([2-[(1-Methylethyl)oxy]ethyl}oxy)-8-(methoxy)-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine

Procedure

To methanol (120 ml) was added sodium (0.966 g). When the metal was dissolved, 8-bromo-2-({2-[(1-methylethyl)oxy]ethyl}oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (5.69 g, 21.2 mmol) was added, heated to reflux and the solution stirred for 16 h, cooled to room temperature. The solvent was removed. Extracted with ethyl acetate after adding water, dried and concentrated to give the crude product which was purified through silica gel eluting with 2:1 ethyl acetate:petroleum ether to give the title compound (4.8 g).

Workup

  1. dissolutionWhen the metal was dissolved
  2. temperatureheated
  3. temperatureto reflux
  4. customThe solvent was removed
  5. extractionExtracted with ethyl acetate
  6. additionafter adding water
  7. customdried
  8. concentrationconcentrated
  9. customto give the crude product which
  10. customwas purified through silica gel eluting with 2:1 ethyl acetate

Sources & evidence

ORD record
ord-9a8e7c41a71e4a0b95d25833b43c1cb7
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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