HCID 67523903, compound → HCID 67523919, compound

HRID 659010Notes

Reaction equation

HRID 659010 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[N:6]=1>C(OCC)(=O)C.[Pd]>[NH2:20][C:18]1[CH:17]=[CH:16][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[N:6]=2)=[C:2]([Cl:1])[CH:19]=1

Participants

4

Reactant 1

HCID 67523903HCID 67523903, compound

Product 1

HCID 67523919HCID 67523919, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.00 g (3.08 mmol) 3-[4-(2-chloro-4-nitro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in a mixture of 30 ml ethyl acetate was hydrogenated over 200 mg palladium on barium sulphate for 10 h. The catalyst was filtered off and the filtrate evaporated. The obtained oil was dissolved in ethyl acetate and purified by chromatography on silica (ethyl acetate) to give 510 mg (56%) of 3-[4-(4-amino-2-chloro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol as colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. dissolutionThe obtained oil was dissolved in ethyl acetate
  4. custompurified by chromatography on silica (ethyl acetate)

Sources & evidence

ORD record
ord-7de18b9eb2b6412eb86812c3a7745fa3
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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