2-Methoxyethanol → [2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011022Notes

Reaction equation

HRID 1011022 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].CC(C)([O-])C.[Na+].Cl[C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)=[C:15]([NH2:28])[N:14]=1>COCCOC>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)=[C:15]([NH2:28])[N:14]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23676156Sodium t-butoxide

Product 1

HCID 57699621[2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
110 °C

Procedure

2-Methoxyethanol (3.2 mL) was diluted with 1,2-dimethoxyethane (20 mL). To this was added sodium tert-butoxide (3.9 g) gradually and the reaction mixture was stirred under nitrogen until it was homogenous. 2-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (2.5376 g) was then added to the reaction mixture, followed by 1,2-dimethoxyethane (20 mL). The reaction mixture was then heated to reflux (110° C., external) overnight. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (100 mL, twice). The combined organic layers were then washed with brine (100 mL). The organic layer was then dried by passing through a hydrophobic frit and then evaporated under reduced pressure (followed by azeotroping with toluene (100 mL, twice)). This gave an amber oil that under high vacuo gave gummy foam. This material was triturated with diethyl ether (with cooling) until this gave the title compound, a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. customThe reaction was quenched with water (100 mL)
  3. extractionextracted with ethyl acetate (100 mL
  4. washThe combined organic layers were then washed with brine (100 mL)
  5. customThe organic layer was then dried
  6. customevaporated under reduced pressure (followed by azeotroping with toluene (100 mL, twice))
  7. customThis gave an amber oil that under high vacuo
  8. customgave gummy foam
  9. customThis material was triturated with diethyl ether (with cooling) until

Sources & evidence

ORD record
ord-0398d19985f846a9b82e0e2e7e83f4ce
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…