HCID 66841025, compound → HCID 58613213, compound

HRID 252979Notes

Reaction equation

HRID 252979 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:16]=[C:15]([NH:17][N:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=2)[CH:14]=[C:13]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd].C(O)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:16]=[C:15]([NH:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=2)[CH:14]=[C:13]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 66841025HCID 66841025, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58613213HCID 58613213, compoundYield 9,600%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 91, N-[2-(2-benzyloxy-ethyl)-6-morpholin-4-yl-pyrimidin-4-yl]-N′-(3-methyl-benzylidene)-hydrazine (109 mg., 0.25 mmol) was dissolved in ethanol (20 mL) and to the solution was added 10% palladium on carbon (200 mg.), three drops of glacial acetic acid, and the reaction was stirred at room temperature under 1 atmosphere of hydrogen for 4 hours. The reaction was passed through celite, evaporated and purified by column chromatography to give Compound 92, N-[2-(2-benzyloxy-ethyl)-6-morpholin-4-yl-pyrimidin-4-yl]-N′-(3-methyl-benzyl)-hydrazine (106 mg., 24 mmol).

Workup

  1. customevaporated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-760f4ee1a3e84f3e972568b32a9ba281
Source dataset
uspto-grants-2011_01
Patent number
US07872005B2

Reaction notes

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