HCID 10708388, compound → HCID 10729495, compound

HRID 1646390Notes

Reaction equation

HRID 1646390 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH2:9][CH2:10][CH3:11])[CH:3]=1>[Pd].C(O)C>[N:12]1([N:8]([CH2:9][CH2:10][CH3:11])[C:4]2[CH:3]=[CH:2][N:7]=[CH:6][N:5]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1

Participants

4

Reactant 1

HCID 10708388HCID 10708388, compound

Product 1

HCID 10729495HCID 10729495, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 100 ml ethanol, was added 10% Pd/C (1.2 g), MgO (1.0 g), and 6-chloro-N-(1H-indol-1-yl)-N-propyl-4-pyrimidinamine (4.2 g). After stirring under H2 at ambient temperature for three hours, the mixture was filtered, and the filtrate evaporated to 4.0 g of an oil. This material was eluted on a silica gel column with 10% ethyl acetate/DCM via HPLC, to give 2.4 g (66%) of an oil, product N-(1H-Indol-1-yl)-N-propyl-4-pyrimidinamine.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated to 4.0 g of an oil
  3. washThis material was eluted on a silica gel column with 10% ethyl acetate/DCM via HPLC

Sources & evidence

ORD record
ord-4bf4df832d3e4b10a2b632819dfcded7
Source dataset
uspto-grants-1993_01
Patent number
US05179204

Reaction notes

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