HCID 67523891, compound → HCID 67524050, compound

HRID 659017Notes

Reaction equation

HRID 659017 reaction equation
[F: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>[Pd].CO>[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]([F:1])[CH:19]=1

Participants

4

Reactant 1

HCID 67523891HCID 67523891, compound

Product 1

HCID 67524050HCID 67524050, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.90 g (9.41 mmol) 3-[4-(2-fluoro-4-nitro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in a mixture of 50 ml TH/methanol 1:1 was hydrogenated over 500 mg 10% Pd/C 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 (dichloromethane/methanol 94:6) to give 1.70 g (65%) of 3-[4-(4-amino-2-fluoro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol.

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 (dichloromethane/methanol 94:6)

Sources & evidence

ORD record
ord-999dc34f67f44c92b88caa1cca519f2f
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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