HCID 86712738, compound → HCID 86712740, compound

HRID 1779112Notes

Reaction equation

HRID 1779112 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1>CN(C=O)C.CO.CCOC(C)=O.[Pt]=O>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1

Participants

6

Reactant 1

HCID 86712738HCID 86712738, compound

Product 1

HCID 86712740HCID 86712740, compound

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-((2,5-dichloropyrimidin-4-yl)ethynyl)phenyl)acetamide (A138) (1.2 g, 4.0 mmol) in DMF (40 mL) and MeOH (8 mL) was stirred with platinum(II)oxide (0.27 g, 1.2 mmol) under an atmosphere of hydrogen for 144 hours at ambient temperature. The reaction mixture was diluted with EtOAc and filtered through a plug of Celite. The solvents were removed in vacuo and the crude residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM) to give the title compound (A139) as a light yellow solid (0.63 g, 51%). LCMS-C: rt 4.82 min; m/z 310 [M+H]+.

Workup

  1. filtrationfiltered through a plug of Celite
  2. customThe solvents were removed in vacuo
  3. customthe crude residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-477ef978d7d44deaad4a21b87f0ecc90
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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