Cesium carbonate → HCID 59486235, compound

HRID 912555Notes

Reaction equation

HRID 912555 reaction equation
Cl[C:2]1[C:3]([C:8]2[CH:13]=[C:12]([S:14][CH3:15])[N:11]=[CH:10][N:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[Cl:16][C:17]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[C:20]([Cl:28])[C:18]=1[NH2:19].C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:16][C:17]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[C:20]([Cl:28])[C:18]=1[NH:19][C:2]1[C:3]([C:8]2[CH:13]=[C:12]([S:14][CH3:15])[N:11]=[CH:10][N:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 59486242HCID 59486242, compoundHCID 594862532,6-Dichloro-3,5-dimethoxyaniline

Product 1

HCID 59486235HCID 59486235, compound

Reagents, catalysts & solvents 2

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

Procedure

A suspension of 4-(3-chloro-pyrazin-2-yl)-6-methylsulfanyl-pyrimidine (37) (200 mg, 0.838 mmol), 2,6-dichloro-3,5-dimethoxyaniline (280 mg, 1.26 mmol), DPEphos (90 mg, 0.167 mmol), palladium (II) acetate (19 mg, 0.085 mmol) and cesium carbonate (546 mg, 1.68 mmol) in dioxane (8 mL) is degassed. After purging with Ar, the vial is sealed by the cap and irradiated at 150° C. for 30 minutes in Smith Synthesizer. The reaction mixture is evaporated and purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 10% to 30% to afford the desired product (2,6-dichloro-3,5-dimethoxy-phenyl)-[3-(6-methylsulfanyl-pyrimidin-4-yl)-pyrazin-2-yl]-amine (38).

Workup

  1. customis degassed
  2. customAfter purging with Ar
  3. customthe vial is sealed by the
  4. customcap
  5. customirradiated at 150° C. for 30 minutes in Smith Synthesizer
  6. customThe reaction mixture is evaporated
  7. custompurified by silica gel flash chromatography
  8. washeluting with ethyl acetate in hexanes from 10% to 30%

Sources & evidence

ORD record
ord-ff74b9381c32424ebef3c05016255295
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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