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

HRID 1181678Notes

Reaction equation

HRID 1181678 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:9][N:10]1[C:15](=[O:16])[CH:14]=[C:13]([NH:17][N:18]=[CH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[NH:12][C:11]1=[O:30].N1CCCCC1.C(O)(=O)C>CN(C)C=O.C(O)(C)C>[CH3:9][N:10]1[C:15](=[O:16])[C:14]2=[C:1]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[N:18]([CH2:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[N:17]=[C:13]2[NH:12][C:11]1=[O:30]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 133894-PyridinecarboxaldehydeHCID 698455281-Naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

Product 1

HCID 1363341135-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 62.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Isonicotinaldehyde (0.87 g) was added to a solution of 1-naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone (2.0 g) in dimethylformamide (66 ml) and isopropanol (16 ml). Piperidine (0.66 ml) was added followed by glacial acetic acid (0.08 ml). The solution was heated at 120° C. for 16 hours. Reaction cooled to room temperature, solids precipitated was filtered, and dried to give the subtitle compound (1.63 g). Mass: 383.93 (M+H).

Workup

  1. customReaction
  2. temperaturecooled to room temperature
  3. customsolids precipitated
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-c54a94afde584aa088343351a0da5805
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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