Cesium carbonate → HCID 57962622, compound

HRID 541907Notes

Reaction equation

HRID 541907 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21](Cl)[N:20]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH:5]=[N:6][CH:7]=1.O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[Cl:25][C:24]1[CH:23]=[N:22][C:21]2[NH:1][C:2]3[CH:7]=[N:6][CH:5]=[C:4]([CH:3]=3)[CH2:8][CH2:9][C:10]3[CH:11]=[C:12]([NH:18][C:19]=1[N:20]=2)[CH:13]=[CH:14][C:15]=3[O:16][CH3:17]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 57962244HCID 57962244, compound

Product 1

HCID 57962622HCID 57962622, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

Into the reaction was added N-{3-[2-(5-aminopyridin-3-yl)ethyl]-4-methoxyphenyl}-2,5-dichloropyrimidin-4-amine (1.75 g, 4.48 mmol), 1,4-dioxane (29 mL), N,N-dimethylformamide (29 mL), palladium acetate (30 mg, 0.1 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (90 mg, 0.2 mmol), and cesium carbonate (2.92 g, 8.97 mmol). The mixture was degassed with N2 bubbling and then microwaved at 150° C. for 20 min. After concentration to remove the solvent, 20 mL of water was added to the residue. The formed precipitate was then collected by vacuum filtration and air dried overnight to give the desired product (1.35 g, 85%). LCMS for C18H17ClN5O (M+H)+: m/z=354.1.

Workup

  1. customThe mixture was degassed with N2 bubbling
  2. custommicrowaved at 150° C. for 20 min
  3. concentrationAfter concentration
  4. customto remove the solvent, 20 mL of water
  5. additionwas added to the residue
  6. filtrationThe formed precipitate was then collected by vacuum filtration and air
  7. customdried overnight

Sources & evidence

ORD record
ord-8b8c80df268b4e21aab1a5327aec608b
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

Loading…