Triethylamine → HCID 58190359, compound

HRID 1972356Notes

Reaction equation

HRID 1972356 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1.C(N(CC)CC)C.O1CCOCC1>O>[Br:15][C:16]1[CH:17]=[N:18][C:19]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C@@H:10]2[CH3:14])=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 6066655-Bromo-2-chloropyrimidineHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 58190359HCID 58190359, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A 250 mL pressure vessel was charged with (S)-4-(tert-butoxycarbonyl)-2-methylpiperazine (4.17 g, 21.84 mmol, Sigma-Aldrich, St. Louis, Mo.), 5-bromo-2-chloropyrimidine (4.22 g, 21.84 mmol, Combi-Blocks, San Diego, Calif.), triethylamine (6.09 mL, 43.7 mmol), and 50 mL of dioxane. The tube was sealed and heated at 110° C. for 24 h. The mixture was diluted with water (100 mL) and extracted with EtOAc (2×150 mL). The organics were dried (MgSO4) and concentrated to give an oil that was purified via column chromatography (120 g silica, 0 to 30% EA/Hex) to give tert-butyl (3S)-4-(5-bromo-2-pyrimidinyl)-3-methyl-1-piperazinecarboxylate (6.15 g) as a white solid.

Workup

  1. customThe tube was sealed
  2. extractionextracted with EtOAc (2×150 mL)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oil that
  6. customwas purified via column chromatography (120 g silica, 0 to 30% EA/Hex)

Sources & evidence

ORD record
ord-b960ca80adb84b99ac607ab529839530
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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