HCID 86618732, compound → HCID 66797956, compound

HRID 447673Notes

Reaction equation

HRID 447673 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH:5]=[C:4]([CH3:18])[N:3]=1.[H][H]>C(O)C.[Pd]>[C@@H:9]1([NH:8][C:6]2[CH:5]=[C:4]([CH3:18])[N:3]=[CH:2][N:7]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 86618732HCID 86618732, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66797956HCID 66797956, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-6-methylpyrimidine-4-amine (1.95 g, 7.5 mmol) was dissolved in ethanol (5 mL) and 10% Pd/C (0.140 g, 0.13 mmol) was added. The flask was filled with hydrogen and stirred overnight. At that time, TLC indicated complete conversion. Palladium was filtered off and the solvent was removed in vacuo. The residue was purified using chromatography on silica gel using gradient 50 to 100% ethyl acetate in hexane to afford the title compound (1.65 g, 93%). LC/MS: Rt=1.51 min, ES+ 226 (AA standard).

Workup

  1. filtrationPalladium was filtered off
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified

Sources & evidence

ORD record
ord-b4be8b71d93c4ce1898540655561544a
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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