Cesium carbonate → 5-(5-acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo(4,3-d)pyrimidin-7-one

HRID 354206Notes

Reaction equation

HRID 354206 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:14]2[NH:15][C:16](=[O:31])[C:17]3[C:18](=[C:20]([CH2:29][CH3:30])[N:21]([CH:23]4[CH2:26][N:25]([CH2:27][CH3:28])[CH2:24]4)[N:22]=3)[N:19]=2)[C:7]([O:10][CH2:11][CH2:12][CH3:13])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[C:32](=O)([O-])[O-].[Cs+].[Cs+]>C(O)CCC>[C:1]([C:4]1[CH:5]=[C:6]([C:14]2[NH:15][C:16](=[O:31])[C:17]3[C:18](=[C:20]([CH2:29][CH3:30])[N:21]([CH:23]4[CH2:26][N:25]([CH2:27][CH3:28])[CH2:24]4)[N:22]=3)[N:19]=2)[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH3:32])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 1354279925-(5-acetyl-2-propoxy-3-pyridinyl)-3-ethyl-2-(1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1355155655-(5-acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo(4,3-d)pyrimidin-7-oneYield 64.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

The title compound from example 119 (120 mg, 0.28 mmol) and cesium carbonate (274 mg, 0.84 mmol) were dissolved in n-butanol (4 ml), and heated at 90° C. under nitrogen with molecular sieves for 96 h. The mixture was then partitioned between water (10 ml) and dichloromethane (10 ml). The organic layer was separated, and the aqueous layer extracted further with dichloromethane (3×15 ml). The combined organic layers were dried (MgSO4), and concentrated in vacuo. The crude product was purified by flash column chromatography (95:5:0.5-90:10:1 ethyl acetate:methanol:0.88 NH3 as eluents), to yield the title compound as a colourless glass (77 mg, 0.18 mmol).

Workup

  1. customThe mixture was then partitioned between water (10 ml) and dichloromethane (10 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted further with dichloromethane (3×15 ml)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (95:5:0.5-90:10:1 ethyl acetate:methanol:0.88 NH3 as eluents)

Sources & evidence

ORD record
ord-ad21f0c1fda241cb92e89617c0147857
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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