Cyclohexene → 1-propyl-8-(1H-pyrazol-4-yl)-1,7-dihydro-purin-6-one

HRID 535984Notes

Reaction equation

HRID 535984 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[N:21](COCC[Si](C)(C)C)[C:20]3[C:19](=[O:30])[N:18]([CH2:31][CH2:32][CH3:33])[C:17](Cl)=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.C1CCCCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:31]([N:18]1[C:19](=[O:30])[C:20]2[NH:21][C:13]([C:11]3[CH:12]=[N:8][NH:9][CH:10]=3)=[N:14][C:15]=2[N:16]=[CH:17]1)[CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 671348358-(1-Benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

Product 1

HCID 469129841-propyl-8-(1H-pyrazol-4-yl)-1,7-dihydro-purin-6-oneYield 36.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-(1-Benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.1 g, 0.201 mmol), Pd(OH)2 (20%) (0.2 g), in ethanol (4 ml) and cyclohexene were stirred under nitrogen balloon for 25 hrs. Reaction mixture was filtered through celite bed washed with methanol (20 ml). The filtrate was concentrated under vacuum and the crude product was purified by column chromatography using silica gel (100-200 mesh) and 5 to 6% methanol in DCM as an eluent to obtain 1-propyl-8-(1H-pyrazol-4-yl)-1,7-dihydro-purin-6-one (0.018 g, 24%) as white solid.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite bed
  3. washwashed with methanol (20 ml)
  4. concentrationThe filtrate was concentrated under vacuum
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cedef7cf57ad4cce9df80733256a8845
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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