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 354177

반응식

HRID 354177 반응식
[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]

참가 물질

5

반응물 2

HCID 1118Sulfuric Acid2회HCID 1357306465-(2-Butoxy-5-ethynyl-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

생성물 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

시약·촉매·용매 2

HCID 24544Mercuric sulfate촉매2회HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-85c03c5f9bee4c9e8e2a10660d651b81
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756373B1

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