Aniline → HCID 66955518, compound

HRID 1399751Notes

Reaction equation

HRID 1399751 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:6]1[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=[C:2]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:7]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955518HCID 66955518, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.300 mmol), aniline (0.033 mL; 0.361 mmol), palladium acetate (2 mg, 0.009 mmol) and xantphos (10 mg; 0.018 mmol) were placed in a 2 mL reaction tube and dissolved in dioxane (1 mL), the tube was purged with argon, sealed and irradiated in a microwave oven at 160° C. for 15 min. The reaction mixture was partitioned between a saturated sodium chloride solution and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane to yield 58 mg (39%) of the title compound as a colorless oil.

Workup

  1. customthe tube was purged with argon
  2. customsealed
  3. customirradiated in a microwave oven at 160° C. for 15 min
  4. customThe reaction mixture was partitioned between a saturated sodium chloride solution and dichloromethane
  5. filtrationfiltered over a phase separator
  6. filtrationfilter (1PS)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane

Sources & evidence

ORD record
ord-93824eed90ec456fbc8726b622305bd5
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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