HCID 123316877, compound → 6-(4-hydroxy-2-methylphenyl)-1,5-dimethyl-3-{[2-(trimethylsilyl)ethoxy]methyl}pyrimidine-2,4(1H,3H)-dione

HRID 514309Notes

Reaction equation

HRID 514309 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]([CH3:21])[C:19](=[O:22])[N:18]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17](=[O:31])[C:16]=2[CH3:32])=[C:11]([CH3:33])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]([CH3:21])[C:19](=[O:22])[N:18]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17](=[O:31])[C:16]=2[CH3:32])=[C:11]([CH3:33])[CH:10]=1

Participants

5

Reactant 2

HCID 123316877HCID 123316877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1239830176-(4-hydroxy-2-methylphenyl)-1,5-dimethyl-3-{[2-(trimethylsilyl)ethoxy]methyl}pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of C4 (10 g, 21 mmol) and palladium hydroxide (2 g, dry) in methanol (300 mL) was stirred at room temperature for 24 hours under 40 psi of hydrogen. After filtration of the reaction mixture, the filtrate was concentrated to provide the product as a light yellow solid. Yield: 8.0 g, 21 mmol, 100%. 1H NMR (400 MHz, CDCl3) δ 6.92 (d, half of AB quartet, J=8.2 Hz, 1H), 6.81-6.87 (m, 2H), 5.52 (AB quartet, JAB=9.5 Hz, ΔνAB=2.7 Hz, 2H), 3.73-3.80 (m, 2H), 3.03 (s, 3H), 2.11 (s, 3H), 1.65 (s, 3H), 0.99-1.05 (m, 2H), 0.01 (s, 9H).

Workup

  1. filtrationAfter filtration of the reaction mixture
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4cd5260ba3244eff9c871ac2d5437bdf
Source dataset
uspto-grants-2015_08
Patent number
US09107923B2

Reaction notes

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