5-[2-Ethoxy-5-(4-ethylpiperazin-1-ylsulphonyl)pyridin-3-yl]-3-ethyl-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one → 3-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-methoxypyridin-3-yl]-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

HRID 990236Notes

Reaction equation

HRID 990236 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:22])[C:13]3[C:14](=[C:16]([CH2:20][CH3:21])[N:17]([CH3:19])[N:18]=3)[N:15]=2)=[CH:8][C:7]([S:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:6][N:5]=1)C>N.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:20]([C:16]1[N:17]([CH3:19])[N:18]=[C:13]2[C:12](=[O:22])[NH:11][C:10]([C:9]3[C:4]([O:3][CH3:1])=[N:5][CH:6]=[C:7]([S:23]([N:26]4[CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH2:31]4)(=[O:24])=[O:25])[CH:8]=3)=[N:15][C:14]=12)[CH3:21]

Participants

4

Reactant 1

HCID 1358163675-[2-Ethoxy-5-(4-ethylpiperazin-1-ylsulphonyl)pyridin-3-yl]-3-ethyl-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1358163333-Ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-methoxypyridin-3-yl]-2-methyl-2,6-dihydro-7h-pyrazolo[4,3-d]pyrimidin-7-oneYield 24%

Reagents, catalysts & solvents 2

HCID 22386232Copper(2+) sulfate heptahydrateCatalystHCID 222AmmoniaSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the title compound of Example 78 (100 mg, 0.21 mmol), and copper (II) sulphate heptahydrate (75 mg, 0.3 mmol) in saturated methanolic ammonia (20 ml) was heated at 100° C. for 4 hours in a sealed vessel. The cooled mixture was evaporated under reduced pressure and the residue suspended in aqueous sodium carbonate solution (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with brine (3×20 ml), dried (Na2SO4) and evaporated under reduced pressure to give a green solid. The crude product was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 97:3) and recrystallised from hexane/ethyl acetate/methanol to afford the title compound (23 mg, 24%) as a white solid. Found : C, 51.22; H, 5.81; N, 20.61. C20H27N7O4S; 0.5H2O requires C, 51.05; H, 6.00; N, 20.84%; δ (CDCl3): 1.07 (3H, t), 1.40 (3H, t), 2.40-2.65 (6H, m), 3.04 (2H, q), 3.19 (4H, m), 4.09 (3H, s), 4.24 (3H, s), 8.65 (1H, s), 9.05 (1H, s), 10.58 (1H, s). LRMS: m/z 462 (M+1)+.

Workup

  1. customThe cooled mixture was evaporated under reduced pressure
  2. extractionextracted with dichloromethane (3×20 ml)
  3. washThe combined organic extracts were washed with brine (3×20 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto give a green solid
  7. customThe crude product was purified by column chromatography on silica gel
  8. customrecrystallised from hexane/ethyl acetate/methanol

Sources & evidence

ORD record
ord-5a87b32823284e7890f9be5da78f1948
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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