1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 57516492, compound

HRID 1912190Notes

Reaction equation

HRID 1912190 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.[Cl:12][C:13]1[N:18]=[C:17]([NH2:19])[C:16]([CH3:20])=[CH:15][N:14]=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.CC(C)([O-])C.[K+]>O1CCOCC1.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:13]1[N:18]=[C:17]([NH:19][C:2]2[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=2)[C:16]([CH3:20])=[CH:15][N:14]=1

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 57516492HCID 57516492, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-bromo-3,5-dimethoxybenzene (436 mg, 2.01 mmol), 2-chloro-5-methyl-pyrimidin-4-ylamine (287 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), Xantphos (237 mg, 0.41 mmol) and potassium tert-butoxide (448 mg, 3.99 mmol) in dioxane (15 mL) and DMF (5 mL) was microwaved at 160° C. for 20 min. The reaction mixture was cooled to room temperature and filtered rinsing with DCM and methanol. The filtrate was concentrated and purified using gradient flash chromatography (0-100% ethyl acetate in hexanes) to afford the title compound as a yellow solid (182 mg, 33%).

Workup

  1. customwas microwaved at 160° C. for 20 min
  2. filtrationfiltered
  3. washrinsing with DCM and methanol
  4. concentrationThe filtrate was concentrated
  5. custompurified

Sources & evidence

ORD record
ord-858b04df23504bb7a41aaec014094ffd
Source dataset
uspto-grants-2013_12
Patent number
US08604042B2

Reaction notes

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