Sulfuric Acid → 5-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354177Notes

Reaction equation

HRID 354177 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([C:12]2[NH:13][C:14](=[O:27])[C:15]3[C:16](=[C:18]([CH2:25][CH3:26])[N:19]([CH2:21][CH2:22][O:23][CH3:24])[N:20]=3)[N:17]=2)=[CH:10][C:9]([C:28]#[CH:29])=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[OH:30]S(O)(=O)=O>CC(C)=O.S([O-])([O-])(=O)=O.[Hg+2]>[C:28]([C:9]1[CH:10]=[C:11]([C:12]2[NH:13][C:14](=[O:27])[C:15]3[C:16](=[C:18]([CH2:25][CH3:26])[N:19]([CH2:21][CH2:22][O:23][CH3:24])[N:20]=3)[N:17]=2)[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[N:7][CH:8]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 1118Sulfuric Acid2×HCID 1357306465-(2-Butoxy-5-ethynyl-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1354846345-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 2

HCID 24544Mercuric sulfateCatalyst2×HCID 180AcetoneSolvent

Procedure

The title compound of Example 15 (2.4 g, 6 mmol) and mercury sulfate (100 mg, 0.34 mmol) were stirred together in a mixture of 1N H2SO4 (5 mL) and acetone (35 mL). After 2 h a further portion of mercury sulfate (100 mg) was added and a third portion (100 mg in 5 mL 1N H2SO4) was added 2 h later. The crude reaction mixture was concentrated and the black residue partitioned between dichloromethane and water. The organic phase was separated and washed with saturated sodium bicarbonate solution and brine, dried (MgSO4) and evaporated. Purification by flash column chromatography (gradient elution from 30% ethyl acetate: pentane to 100% ethyl acetate) gave 780 mg product.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. customthe black residue partitioned between dichloromethane and water
  4. customThe organic phase was separated
  5. washwashed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customPurification
  9. washby flash column chromatography (gradient elution from 30% ethyl acetate: pentane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-85c03c5f9bee4c9e8e2a10660d651b81
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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