Cyclopropaneethanamine → HCID 57699835, compound

HRID 1011044Notes

Reaction equation

HRID 1011044 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.[CH:18]1([CH2:21][CH2:22][NH2:23])[CH2:20][CH2:19]1>C(O)CO.C(OCC)(=O)C>[CH:18]1([CH2:21][CH2:22][NH:23][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)=[C:4]([NH2:17])[N:3]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 10240761CyclopropaneethanamineHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenine

Product 1

HCID 57699835HCID 57699835, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (3.49 g) in ethylene glycol (17 ml) at room temperature was added cyclopropylethylamine (4.69 g). The reaction mixture was heated to 120° C. with reflux condenser overnight, resulting in a yellow/brown solution. The reaction was allowed to cool, taken up in ethyl acetate (100 ml) and washed with water (2×100 ml). The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to give a dark brown gum (4.17 g)

Workup

  1. temperaturewith reflux condenser overnight
  2. customresulting in a yellow/brown solution
  3. temperatureto cool
  4. washwashed with water (2×100 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cebd60ae6d5f48c09b4237e36bf56bc7
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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