4-Aminophenol → HCID 67242656, compound

HRID 2422328Notes

Reaction equation

HRID 2422328 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:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[OH:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][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 4034-AminophenolHCID 81531DiisopropylethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 53592776-Chloropurine

Product 1

HCID 67242656HCID 67242656, 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 (1309 mg) of 4-hydroxyphenylamine (4-hydroxyaniline) and 4 ml of N-ethyldiisopropylamine was refluxed in n-butanol for 3 hrs. After removal of the n-butanol 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 ether. The solid residue was filtered off and the crude product crystallized from methanol. Yield: 90%, white solid. TLC (CHCl3:CH3OH:NH3) (90:10:0.1) (v:v): single spot; HPLC: purity >98%. 1H NMR (400 MHz, DMSO): 1.56tt (2H, Ja=11.0 Hz, Jb=3.3 Hz); 1.72qq (1H, Ja=11.6 Hz, Jb=3.3 Hz); 1.94tt (2H, Ja=11.0 Hz, Jb=3.3 Hz); 2.28qq (1H, Ja=11.6 Hz, Jb=3.3 Hz); 3.66m (1H); 3.98dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 5.62dd (1H, Ja=11.0 Hz, Jb=2.1 Hz); 7.02d (2H, J=8.5 Hz); 8.19s (1H); 8.26d (2H, J=8.5 Hz); 8.29s (1H); 8.95s (1H). MS (ES+): [M+H]+=312 (100).

Workup

  1. customAfter removal of the n-butanol
  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 ether
  7. filtrationThe solid residue was filtered off
  8. customthe crude product crystallized from methanol
  9. custom8.19s (1H)
  10. custom8.29s (1H)
  11. custom8.95s (1H)

Sources & evidence

ORD record
ord-060cc46841eb4920985f27ba41b3cf43
Source dataset
uspto-grants-2011_06
Patent number
US07960397B2

Reaction notes

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