2-(1-Azidoethyl)-5-fluoropyrimidine → 1-(5-Fluoropyrimidin-2-yl)ethan-1-amine

HRID 415417Notes

Reaction equation

HRID 415417 reaction equation
[N:1]([CH:4]([C:6]1[N:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[CH3:5])=[N+]=[N-]>[Pd]>[F:12][C:9]1[CH:8]=[N:7][C:6]([CH:4]([NH2:1])[CH3:5])=[N:11][CH:10]=1

Participants

3

Reactant 1

HCID 509937232-(1-Azidoethyl)-5-fluoropyrimidine

Product 1

HCID 509948141-(5-Fluoropyrimidin-2-yl)ethan-1-amineYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round-bottom flask containing 2-(1-azidoethyl)-5-fluoropyrimidine (Method 3, 0.60 g, 3.59 mmol) was charged with 10% Pd/C (0.191 g) and was evacuated and backfilled with H2 via a filled balloon. MeOH (10 ml) was added, and the mixture was allowed to stir at room temperature for 3 hours. The mixture was filtered through a plug of diatomaceous earth, which was subsequently washed well with MeOH. The filtrates were concentrated to give the title compound as a pale yellow oil (0.50 g, 99%). 1H NMR (CDCl3) δ 8.60 (s, 2H), 4.65 (br s 2H), 4.10 (m, 1H), 1.20 (d, 3H).

Workup

  1. customwas evacuated
  2. additionMeOH (10 ml) was added
  3. filtrationThe mixture was filtered through a plug of diatomaceous earth, which
  4. washwas subsequently washed well with MeOH
  5. concentrationThe filtrates were concentrated

Sources & evidence

ORD record
ord-0f9993312b8f447b9a64c7f2ca1fdee8
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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