Triethylamine → HCID 44129341, compound

HRID 2036323Notes

Reaction equation

HRID 2036323 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][CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31].C(N(CC)CC)C>C(O)CC>[OH:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH:31][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

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 702672-(Aminomethyl)phenolHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 53592776-Chloropurine

Product 1

HCID 44129341HCID 44129341, compoundYield 90%

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) 2-hydroxybenzylamine, and 5 mL of triethylamine was refluxed in n-propanol for 3 hrs. 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 90%, white solid. TLC (EtOAc:hexane (1:1) (v:v): single spot; HPLC: purity>98%. 1H-NMR (400 MHZ, DMSO): 1.58m (2H); 1.70m (1H); 1.95m (2H); 2.26qq (1H, Ja=11.8 Hz, Jb=4.0 Hz); 3.67m (1H); 4.0d (1H, J=11.3 Hz); 4.64bs (2H); 5.63dd (1H, Ja=11.3 Hz, Jb=1.8 Hz); 6.73t (1H, J=7.5 Hz); 6.82 (d, 1H, J=7.9 Hz); 7.06t (1H, J=7.5 Hz); 7.14d (1H, J=7.5 Hz); 8.21s (1H); 8.35bs (1H); 8.37bs (1H); 9.82bs (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. custom8.21s (1H)

Sources & evidence

ORD record
ord-26e01ca17fae4b53b80376b2836d5837
Source dataset
uspto-grants-2013_11
Patent number
US08575182B2

Reaction notes

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