Cesium carbonate → HCID 86668828, compound

HRID 921451Notes

Reaction equation

HRID 921451 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH2:9])[N:5]=[N:6][C:7]=1[CH3:8].CP([C:14]1[CH:20]=[CH:19][C:17](N)=[C:16]([S:21](C(C)C)(=[O:23])=[O:22])[CH:15]=1)(C)=O.C[C:28]1([CH3:68])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.[C:69](=[O:72])([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:9][C:20]2[CH:19]=[CH:17][C:16]([S:21]([N:6]3[CH2:68][CH2:28][N:3]([CH3:4])[CH2:2][CH2:7]3)(=[O:22])=[O:23])=[CH:15][C:14]=2[O:72][CH3:69])[N:5]=[N:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 45076018HCID 45076018, compoundHCID 67052708HCID 67052708, compound

Product 1

HCID 86668828HCID 86668828, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-chloro-6-methyl-1,2,4-triazin-3-amine (2.00 mmol) in 8 mL toluene is added 4-(dimethylphosphoryl)-2-(propan-2-ylsulfonyl)aniline (2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and cesium carbonate (2.20 mmol). The mixture is purged with nitrogen, and can be subjected to microwaves at 100° C. until formation of the desired product. The reaction mixture can then be concentrated and purified by silica gel chromatography.

Workup

  1. customThe mixture is purged with nitrogen
  2. customcan be subjected to microwaves at 100° C. until formation of the desired product
  3. concentrationThe reaction mixture can then be concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-00fc7834c7b24683bb8dfebc0eef5f51
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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