Acetic Acid → HCID 135730592, compound

HRID 354202Notes

Reaction equation

HRID 354202 reaction equation
[CH:1]1([O:5][C:6]2[C:11]([C:12]3[NH:13][C:14](=[O:25])[C:15]4[N:20]([CH3:21])[N:19]=[C:18]([CH2:22][CH2:23][CH3:24])[C:16]=4[N:17]=3)=[CH:10][C:9]([N+:26]([O-])=O)=[CH:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1.[C:29](O)(=[O:31])[CH3:30]>[Pd]>[NH2:26][C:9]1[CH:10]=[C:11]([C:12]2[NH:13][C:14](=[O:25])[C:15]3[N:20]([CH3:21])[N:19]=[C:18]([CH2:22][CH2:23][CH3:24])[C:16]=3[N:17]=2)[C:6]([O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[N:7][CH:8]=1.[CH:1]1([O:5][C:6]2[N:7]=[CH:8][C:9]([NH:26][C:29](=[O:31])[CH3:30])=[CH:10][C:11]=2[C:12]2[NH:13][C:14](=[O:25])[C:15]3[N:20]([CH3:21])[N:19]=[C:18]([CH2:22][CH2:23][CH3:24])[C:16]=3[N:17]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 135673969HCID 135673969, compound

Product 2

HCID 135730592HCID 135730592, compoundHCID 135730606HCID 135730606, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound from example 88 (266 mg, 0.69 mmol) was dissolved in glacial acetic acid (10 ml) and the vessel charged with 5% Pd on carbon (20 mg) and stirred under hydrogen (60 psi) for 14 h. The catalyst was removed by filtration (Arbocel*) and the residue concentrated in vacuo. The residue was taken up in water (5 ml), basified to pH 8 (5% NaHCO3 solution) and extracted with methylene chloride (3×20 ml). Combined organic extracts were washed with brine (20 ml), dried over MgSO4, reduced in vacuo and purified by column chromatography (first with 98:2 methylene chloride:methanol as eluant, then 30:70:1 ethyl acetate:pentane:0.88 ammonia). 5-[5-amino-2-(cyclobutyloxy)-3-pyridinyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one was obtained (70 mg, 0.19 mmol) together with N-[6-(cyclobutyloxy)-5-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-3-pyridinyl]acetamide (34 mg, 0.09 mmol).

Workup

  1. customThe catalyst was removed by filtration (Arbocel*)
  2. concentrationthe residue concentrated in vacuo
  3. extractionextracted with methylene chloride (3×20 ml)
  4. washCombined organic extracts were washed with brine (20 ml)
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography (first with 98:2 methylene chloride

Sources & evidence

ORD record
ord-0e602412d6ee4c9ab5ff8228d6b2d995
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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