Triethylamine → 6-(4-Hydroxy-3-methoxybenzylamino)-9-(tetrahydrofuran-2-yl)-purine

HRID 2422332

Reaction equation

HRID 2422332 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[CH2:15][CH2:14][CH2:13][O:12]1.ClC1N=CN=C2C=1NC=N2.[OH:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][C:28]=1[O:35][CH3:36].C(N(CC)CC)C>C(O)CC>[OH:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][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[CH2:15][CH2:14][CH2:13][O:12]2)=[CH:29][C:28]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70966VanillylamineHCID 2394846-chloro-9-(tetrahydrofuran-2-yl)-9H-purineHCID 53592776-Chloropurine

Product 1

HCID 441295036-(4-Hydroxy-3-methoxybenzylamino)-9-(tetrahydrofuran-2-yl)-purineYield 80%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 10 mmol (2240 mg) of 6-chloro-9-(tetrahydrofuran-2-yl)-purine (prepared from 10 mmol (1546 mg) of 6-chloropurine), 12 mmol (1838 mg) of 4-hydroxy-3-methoxybenzylamine 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 phase was evaporated and the residuum subsequently washed with 30 ml of petroleum ether. 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): 0.90d (3H, J=6.6 Hz); 1.32m (1H); 1.57m (1H); 1.84m (1H); 1.95m (1H); 2.12m (2H); 2.29m (1H); 3.26m (1H); 3.51bs (2H); 3.73m (1H); 3.89m (1H); 4.40t (1H, J=5.1 Hz); 6.12d (1H, J=5.2 Hz); 7.74bs (1H); 8.18s (1H); 8.28s (1H. MS (ES): [M+H]+=342 (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 phase was evaporated
  6. washthe residuum subsequently washed with 30 ml of petroleum ether
  7. filtrationThe solid residue was filtered off
  8. customthe crude product crystallized from methanol
  9. custom8.18s (1H)
  10. custom8.28s

Sources & evidence

ORD record
ord-9ede13ba21334fbe94484a20fb232391
Source dataset
uspto-grants-2011_06
Patent number
US07960397B2

Linked notes

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