HCID 67958162, compound → HCID 71603517, compound

HRID 527649Notes

Reaction equation

HRID 527649 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([O:10][C:11]2[C:16]3[C:17]([CH3:21])([CH3:20])[CH2:18][O:19][C:15]=3[C:14]([CH3:22])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O>C1COCC1.[Pd]>[CH3:20][C:17]1([CH3:21])[C:16]2[C:11]([O:10][C:7]3[N:6]=[CH:5][C:4]([NH2:1])=[CH:9][N:8]=3)=[CH:12][CH:13]=[C:14]([CH3:22])[C:15]=2[O:19][CH2:18]1

Participants

4

Reactant 1

HCID 67958162HCID 67958162, compound2×

Product 1

HCID 71603517HCID 71603517, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-nitro-2-[(3,3,7-trimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]pyrimidine (Intermediate 189, 243 mg, 0.81 mmol) was dissolved in THF (4 mL) and Palladium on charcoal (5 mol %, 85 mg) was added. The reaction mixture was stirred under hydrogen atmosphere (3 bar) for 1 hour at room temperature. The catalyst was filtered on a pad of celite, washed with THF and the resulting solution was concentrated under vacuum. The residue was diluted with ethyl acetate and water, the organic phase collected, dried over Na2SO4 and evaporated to afford the title compound (220 mg) as colorless oil. The crude product, was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered on a pad of celite
  2. washwashed with THF
  3. concentrationthe resulting solution was concentrated under vacuum
  4. additionThe residue was diluted with ethyl acetate and water
  5. customthe organic phase collected
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-199293ab60a948659cacb73cc3ef8adf
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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