Acetic Acid → 7-isobutyl-2-(1-naphthylmethyl)-3-pyridin-4-yl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 1181684Notes

Reaction equation

HRID 1181684 reaction equation
[CH2:1]([N:5]1[C:10]([NH:11][N:12]=[CH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:9][C:8](=[O:24])[NH:7][C:6]1=[O:25])[CH:2]([CH3:4])[CH3:3].[CH:26](=O)[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.N1CCCCC1.C(O)(=O)C>CN(C)C=O.C(O)(C)C>[CH2:1]([N:5]1[C:10]2=[N:11][N:12]([CH2:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[C:26]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[C:9]2[C:8](=[O:24])[NH:7][C:6]1=[O:25])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 133894-PyridinecarboxaldehydeHCID 865954271-Naphthaldehyde (3-isobutyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

Product 1

HCID 694274457-isobutyl-2-(1-naphthylmethyl)-3-pyridin-4-yl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 76.3%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

1-naphthaldehyde (3-isobutyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone (3.4 g) was dissolved in a solution of dimethylformamide (99 ml) and isopropanol (24 ml). isonicotinaldehyde (1.3 g) was added followed by piperidine (0.99 ml) and acetic acid (0.12 ml) The mixture was stirred at room temperature for 18 hours. Solvents were removed under reduced pressure. Crude residue was crystallized in methanol/water to give the title compound (3.28 g). Mass: 425.95 (M+H).

Workup

  1. customSolvents were removed under reduced pressure
  2. customCrude residue was crystallized in methanol/water

Sources & evidence

ORD record
ord-ad24b241889d490285a97d341098509d
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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