HCID 67538861, compound → HCID 67539570, compound

HRID 1192325Notes

Reaction equation

HRID 1192325 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([O:20]CC3C=CC=CC=3)=[CH:18][N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:19]([OH:20])=[CH:18][N:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67538861HCID 67538861, compound

Product 1

HCID 67539570HCID 67539570, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(5-benzyloxypyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.540 g, 1.46 mmol) in MeOH (20 mL) under N2 was cautiously added 10% Pd on carbon (40 mg). The reaction vessel was evacuated under vacuum and then put under an atmosphere of hydrogen using a balloon. The mixture was stirred for 2 hours at room temperature. At this time the hydrogen gas was evacuated and the catalyst was removed by filtration. The filtrate was concentrated. The residue was purified by flash chromatography (1:1 hexanes/EtOAc) to give 4-(5-Hydroxypyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.390 g, 95%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.18 (s, 1H), 7.75 (s, 1H), 3.93 (m, 4H), 3.54 (m, 4H), 1.41 (s, 9H). LCMS (APCI+) m/z 281 [M+H]+; Rt=2.01 minutes.

Workup

  1. customThe reaction vessel was evacuated under vacuum
  2. customAt this time the hydrogen gas was evacuated
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified by flash chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-dcda014181a84baa8c52462add847ebc
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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