1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 118092945, compound

HRID 2207416Notes

Reaction equation

HRID 2207416 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:8]=1)[NH2:5].Cl[C:16]1[N:21]=[C:20]([O:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[CH:19]=[CH:18][N:17]=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.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:16]2[N:21]=[C:20]([O:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)[CH:19]=[CH:18][N:17]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:8]=1

Participants

7

Reactant 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 71629906tert-Butyl 4-((2-chloropyrimidin-4-yl)oxy)piperidine-1-carboxylateHCID 916190751520003-76-2

Product 1

HCID 118092945HCID 118092945, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

3-Methyl-5-(pyridin-3-yl)aniline (50.7 mg, 0.275 mmol) was added a solution of tert-Butyl 4-[(2-chloropyrimidin-4-yl)oxy]piperidine-1-carboxylate (72.0 mg, 0.229 mmol) in dioxane (486 μL). The reaction mixture was flushed and purged with Ar(g) followed by the addition of Pd(OAc)2 (5.15 mg, 0.023 mmol) and Xantphos (19.9 mg, 0.034 mmol). The reaction was heated to 75° C. overnight and then cooled to room temperature. The reaction mixture was diluted with water and extracted with dichloromethane. The organic was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% MeOH in DCM:hexanes, 10:90 to 50:50) to yield tert-butyl 4-[(2-{[3-methyl-5-(pyridin-3-yl)phenyl]amino}pyrimidin-4-yl)oxy]piperidine-1-carboxylate.

Workup

  1. customThe reaction mixture was flushed
  2. custompurged with Ar(g)
  3. temperaturecooled to room temperature
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic was dried over sodium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (10% MeOH in DCM:hexanes, 10:90 to 50:50)

Sources & evidence

ORD record
ord-915e0104bd264aa191b14a3ef5055dfa
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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