Triethylamine → 3-[5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid

HRID 1181680Notes

Reaction equation

HRID 1181680 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][N:10]=[CH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[NH:4][C:3]1=[O:22].C(N(CC)CC)C.[CH:30]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35]([OH:37])=[O:36])=O>CN(C)C=O>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:30]([C:32]3[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=3)[C:35]([OH:37])=[O:36])[N:10]([CH2:11][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[N:9]=[C:5]2[NH:4][C:3]1=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120773-CarboxybenzaldehydeHCID 698455281-Naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

Product 1

HCID 1363341153-[5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone (2.12 g) and triethylamine (0.8 ml) was added to a suspension of Resin bound 3-formylbenzoic acid in dimethylformamide (15 ml), and the mixture was shaken at 90° C. for 16 hours. The resin was filtered and washed (3 times) DMF, CH2Cl2, MeOH, CH2Cl2, and dried in vacuum to give the subtitle compound.

Workup

  1. filtrationThe resin was filtered
  2. washwashed (3 times) DMF, CH2Cl2, MeOH, CH2Cl2
  3. customdried in vacuum

Sources & evidence

ORD record
ord-d0dd19257cd84a4faa51d8b762041751
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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