Potassium Carbonate → 5-[2-Butoxy-5-(2-furyl)-3-pyridinyl]-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354173Notes

Reaction equation

HRID 354173 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1B(O)O.[CH2:15]([O:19][C:20]1[C:25]([C:26]2[NH:27][C:28](=[O:41])[C:29]3[C:30](=[C:32]([CH2:39][CH3:40])[N:33]([CH2:35][CH2:36][O:37][CH3:38])[N:34]=3)[N:31]=2)=[CH:24][C:23](I)=[CH:22][N:21]=1)[CH2:16][CH2:17][CH3:18]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([O:19][C:20]1[C:25]([C:26]2[NH:27][C:28](=[O:41])[C:29]3[C:30](=[C:32]([CH2:39][CH3:40])[N:33]([CH2:35][CH2:36][O:37][CH3:38])[N:34]=3)[N:31]=2)=[CH:24][C:23]([C:8]2[O:7][CH:11]=[CH:10][CH:9]=2)=[CH:22][N:21]=1)[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 1354560315-(2-Butoxy-5-iodo-3-pyridinyl)-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1363883795-[2-Butoxy-5-(2-furyl)-3-pyridinyl]-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 69.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Pd(PPh3)4 (46.5 mg, 0.04 mmol) was added to a stirred mixture of potassium carbonate (55 mg, 0.40 mmol), 2-furylboronic acid (54 mg, 0.48 mmol) and the title compound of Example 1 (200 mg, 0.40 mmol) in degassed dioxan/water (10 mL of 4:1 mixture). The mixture was heated at reflux for 2 h and cooled. The solvent was removed in vacuo and the residue triturated with ethyl acetate to give an orange solid. Purification by flash column chromatography (elution with 50:1 dichloromethane/methanol) gave the title compound as a cream solid (121 mg, 58%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. customThe solvent was removed in vacuo
  5. customthe residue triturated with ethyl acetate
  6. customto give an orange solid
  7. customPurification
  8. washby flash column chromatography (elution with 50:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-62af971fda8f459baa0730747a0f9432
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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