Dichloromethane → HCID 59252645, compound

HRID 1616307Notes

Reaction equation

HRID 1616307 reaction equation
[CH3:1][C@@H:2]([NH2:6])[CH2:3][CH2:4][CH3:5].ClCCl.F[C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:13]([NH2:26])[N:12]=1>C(O)CO>[CH3:1][C@@H:2]([NH:6][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:13]([NH2:26])[N:12]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6994377HCID 6994377, compoundHCID 592525662-Fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 59252645HCID 59252645, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
110 °C

Procedure

A crude sample of (2R)-2-pentanamine containing dichloromethane (11.12 g containing ca 3.1 g, 35.6 mmol of amine) was added to a suspension of 2-fluoro -9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (5.00 g, 21.08 mmol) in ethylene glycol (50 ml). The mixture was heated at 110° C. for 20 hours and then cooled to room temperature and partitioned between water (200 ml) and ethyl acetate (200 ml). The organic phase was separated, washed with saturated brine, dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was dissolved in dichloromethane and purified on a 110 g aminopropyl (NH2) cartridge using a 0-100% ethyl acetate-cyclohexane gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo and the residue triturated with diethyl ether and some insoluble starting material removed by filtration. Evaporation of the ether filtrate afforded the title compound as an off-white foam (2.34 g).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water (200 ml) and ethyl acetate (200 ml)
  3. customThe organic phase was separated
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue was dissolved in dichloromethane
  9. custompurified on a 110 g aminopropyl (NH2) cartridge
  10. customover 40 mins
  11. customevaporated in vacuo
  12. customthe residue triturated with diethyl ether
  13. customremoved by filtration
  14. customEvaporation of the ether filtrate

Sources & evidence

ORD record
ord-8d3fa01cc4ef4b7e926a92398ba174e0
Source dataset
uspto-grants-2014_07
Patent number
US08765772B2

Reaction notes

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