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3-(3,4,5-Trimethoxyphenyl)acrylic acid → 3-Propyl-8-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-3,7-dihydro-purine-2,6-dione

HRID 1292425
Notes
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Reaction equation

HRID 1292425 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=1[NH2:8].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH:49]=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[CH:44]=[CH:45][C:46](O)=O>CN(C)C=O>[CH2:9]([N:6]1[C:7]2[N:8]=[C:46](/[CH:45]=[CH:44]/[C:43]3[CH:49]=[C:50]([O:54][CH3:55])[C:51]([O:52][CH3:53])=[C:41]([O:40][CH3:39])[CH:42]=3)[NH:1][C:2]=2[C:3](=[O:13])[NH:4][C:5]1=[O:12])[CH2:10][CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 106313415,6-Diamino-1-propyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 151708643-Propyl-8-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-3,7-dihydro-purine-2,6-dioneYield 60%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

5,6-Diamino-1-propyluracil (2.00 g, 11 mmol) was suspended in 40 ml of N,N-dimethylformamide. To the suspension were added 3.37 g (16 mmol) of N,N'-dicyclohexylcarbodiimide and 2.00 g (13 mmol) of 1-hydroxybenzotriazole. Then, 2.59 g (11 mmol) of 3,4,5-trimethoxycinnamic acid was slowly added thereto in several portions, and the mixture was stirred overnight at room temperature. After insoluble substances were removed by filtration, the filtrate was concentrated under reduced pressure and 40 ml of a 2N aqueous solution of sodium hydroxide was added to the residue. The mixture was heated under reflux for 30 minutes, followed by neutralization. Deposited crystals were collected by filtration and recrystallized from isopropanol/water to give 2.51 g (overall yield: 60%) of Compound 22 as a yellow powder.

Workup

  1. customAfter insoluble substances were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure and 40 ml of a 2N aqueous solution of sodium hydroxide
  3. additionwas added to the residue
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 30 minutes
  6. filtrationDeposited crystals were collected by filtration
  7. customrecrystallized from isopropanol/water

Sources & evidence

ORD record
ord-038f24034db9491a8186406b565c0add
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05756735

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes