2,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine → 5-Isopropyl-6-(2,3,5-trimethyl-phenoxy)-1H-pyrimidine-2,4-dione

HRID 426260Notes

Reaction equation

HRID 426260 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[C:11]([O:26][C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[C:28]=2[CH3:35])[N:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[CH:23]([C:12]1[C:13](=[O:15])[NH:14][C:9](=[O:8])[NH:10][C:11]=1[O:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[C:28]=1[CH3:35])([CH3:25])[CH3:24]

Participants

6

Reactant 2

HCID 591848362,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 591848065-Isopropyl-6-(2,3,5-trimethyl-phenoxy)-1H-pyrimidine-2,4-dioneYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine was dissolved in 6 mL ethyl acetate and 6 mL ethanol mixture. 10% Pd/C (52 mg) was added to the mixture. Then hydrogen balloon was applied. The reaction was stirred at room temperature for 40 minutes. The reaction crude was filtered through celite. The filtrate was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) followed by reverse phase HPLC (MeCN/water) to give white solid (94 mg, 59%). LC-MS shows 289.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 9.6 (br, 1H), 8.9 (br, 1H), 6.88 (s, 1H), 6.58 (s, 1H), 3.12 (m, 1H), 2.18 (s, 6H), 2.12 (s, 3H), 1.22 (d, 6H).

Workup

  1. customThe reaction crude
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated down
  4. custompurified (silica gel, 0-50% EtOAC/hexane)

Sources & evidence

ORD record
ord-d55aaa821c174f1888650d07e3e8dba9
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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