Triethylamine → HCID 44582130, compound

HRID 2036322Notes

Reaction equation

HRID 2036322 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:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32].C(N(CC)CC)C>C(O)CCC>[OH:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH:32][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 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 7358943-(Aminomethyl)phenolHCID 53592776-Chloropurine

Product 1

HCID 44582130HCID 44582130, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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) 3-hydroxybenzylamine, and 5 mL of triethylamine was refluxed in n-butanol for 3 hours. After removal of the n-butanol by vacuum evaporation water was added to remove the n-butanol residues. The resulting material was treated with water and partitioned into ethyl acetate. The ethyl acetate phase 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>99%. 1H-NMR (400 MHZ, DMSO): 1.57m (2H); 1.70m (1H); 1.95m (2H); 2.27qq (1H, Ja=11.7 Hz, Jb=4.0 Hz); 3.66m (1H); 4.0d (1H); 4.63bs (2H); 5.67dd (1H, Ja=11.3 Hz, Jb=1.8 Hz); 6.58dd (1H, Ja=8.2 Hz, Jb=1.5 Hz); 6.73 (d, 1H, J=7.7 Hz); 7.07t (1H, J=7.7 Hz); 8.21s (1H); 8.33bs (1H); 8.36bs (1H); 9.26s (1H). MS (ES): [M+H]+=326 (100).

Workup

  1. customAfter removal of the n-butanol
  2. customby vacuum evaporation water
  3. additionwas added
  4. customto remove the n-butanol residues
  5. additionThe resulting material was treated with water
  6. custompartitioned into ethyl acetate
  7. customThe ethyl acetate phase was evaporated
  8. washthe residuum subsequently washed with 30 ml of diethylether
  9. filtrationThe solid residue was filtered off
  10. customthe crude product crystallized from methanol
  11. custom8.21s (1H)
  12. custom9.26s (1H)

Sources & evidence

ORD record
ord-cb2ceb64ca914048b9ecfddf09e16ae9
Source dataset
uspto-grants-2013_11
Patent number
US08575182B2

Reaction notes

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