HCID 67524185, compound → HCID 67524085, compound

HRID 658995Notes

Reaction equation

HRID 658995 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[N:10]=2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.CO.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[N:10]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 67524185HCID 67524185, compound

Product 1

HCID 67524085HCID 67524085, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.66 g (29.8 mmol) 3-[4-(4-Nitro-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in a mixture of 173 ml THF and 173 ml methanol was hydrogenated over 3.46 g of 10% palladium on charcoal for 8 h. The catalyst was filtered off and the filtrate evaporated. The obtained oil was treated with a small amount of THF and the precipitate removed by filtration. Evaporation of the filtrate gave an oil that was purified by chromatography on silica (dichloromethane/ethanol 95:5) to give 5.77 g (74%) of 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol as colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. additionThe obtained oil was treated with a small amount of THF
  4. customthe precipitate removed by filtration
  5. customEvaporation of the filtrate
  6. customgave an oil that
  7. customwas purified by chromatography on silica (dichloromethane/ethanol 95:5)

Sources & evidence

ORD record
ord-69d3ded19fc8479bafb84e84791dc7ef
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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