tert-Butyl piperazine-1-carboxylate → HCID 178452260, compound

HRID 522681Notes

Reaction equation

HRID 522681 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CC(O)C.C(N(C(C)C)CC)(C)C>[Br:1][C:2]1[C:3]([OH:9])=[N:4][C:5]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 178517822HCID 178517822, compound

Product 1

HCID 178452260HCID 178452260, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 5-bromo-2-chloropyrimidin-4-ol (6.5 g, 31 mmol), tert-butyl piperazine-1-carboxylate (6.5 g, 35 mmol) in propan-2-ol (200 mL) and diisopropylethylamine (10 mL) was stirred at 80° C. overnight. The mixture was cooled to RT and then concentrated. The residue was purified by silica gel chromatography eluting with ethyl acetate:petroleum ether (100:1) to give tert-butyl 4-(5-bromo-4-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (9 g, 80%) as a yellow solid. MS (ES+) C13H19BrN4O3 requires: 358, 360, found: 303, 305 [M+H-56]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with ethyl acetate:petroleum ether (100:1)

Sources & evidence

ORD record
ord-ed6b88eb75164f74b9698cfb28ada705
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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