Triethylamine → 1144854-41-0

HRID 2422323Notes

Reaction equation

HRID 2422323 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.ClC1N=CN=C2C=1NC=N2.[OH:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C(N(CC)CC)C>C(O)CC>[OH:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 974724-HydroxybenzylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 53592776-Chloropurine

Product 1

HCID 441293451144854-41-0Yield 80%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 10 mmol (2387 mg) 6-chloro-9-(tetrahydropyran-2-yl)purine (prepared from 10 mmol (1546 mg) of 6-chloropurine), 12 mmol (1478 mg) 4-hydroxybenzylamine, and 5 mL of triethylamine was refluxed in n-propanol for 3 hours. After removal of the n-propanol by vacuum evaporation, the resulting material was treated with water and extracted into ethyl acetate. The ethyl acetate solvent was evaporated and the residuum subsequently washed with 30 ml of diethylether. The solid residue was filtered off and the crude product crystallized from methanol. Yield 80%, white solid. TLC (EtOAc:hexane (1:1) (v:v): single spot; HPLC: purity >98%. 1H-NMR (400 MHZ, DMSO): 1.57tt (2H, Ja=11.0 Hz, Jb=3.3 Hz); 1.72qq (1H, Ja=12 Hz, Jb=3.3 Hz); 1.95tt (2H, Ja=11 Hz, Jb=2.1 Hz); 2.27qq (1H, Ja=12.0 Hz, Jb=3.3 Hz); 3.67m (1H); 4.0dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 4.6s (2H); 5.63dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 6.67d (2H, J=8.4Hz); 7.15d (2H, J=8.4 Hz); 8.02bs (1H); 8.21s (1H); 8.33s (1H); 9.21s (1H). MS (ES): [M+H]+=326 (100).

Workup

  1. customAfter removal of the n-propanol
  2. customby vacuum evaporation
  3. additionthe resulting material was treated with water
  4. extractionextracted into ethyl acetate
  5. customThe ethyl acetate solvent was evaporated
  6. washthe residuum subsequently washed with 30 ml of diethylether
  7. filtrationThe solid residue was filtered off
  8. customthe crude product crystallized from methanol
  9. custom4.6s (2H)
  10. custom8.21s (1H)
  11. custom8.33s (1H)
  12. custom9.21s (1H)

Sources & evidence

ORD record
ord-a0c96fb9c6e34b8ea972e2de875b4341
Source dataset
uspto-grants-2011_06
Patent number
US07960397B2

Reaction notes

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