Potassium Carbonate → 4-[5-(2-Butynylamino)-6-methylamino-pyrimidine-4-yl]piperazine-1-carboxylic acid t-butyl ester

HRID 2112926Notes

Reaction equation

HRID 2112926 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([NH2:20])=[C:18]([NH:21][CH3:22])[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]#[C:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:19]([NH:20][CH2:24][C:25]#[C:26][CH3:27])=[C:18]([NH:21][CH3:22])[N:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 27568621-Bromo-2-butyneHCID 150167034-(5-Amino-6-methylamino-pyrimidin-4-yl)piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 576428434-[5-(2-Butynylamino)-6-methylamino-pyrimidine-4-yl]piperazine-1-carboxylic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-Amino-6-methylamino-pyrimidin-4-yl)piperazine-1-carboxylic acid t-butyl ester (200 mg) was dissolved in N,N-dimethylformamide (5.0 mL), and then 1-bromo-2-butyne (57 μL) and anhydrous potassium carbonate (107 mg) were added to this solution. The reaction solution was stirred at room temperature for 20 hours, and then poured into a saturated aqueous ammonium chloride solution. It was then extracted with ethyl acetate, and the obtained organic layer was washed with water and saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (118 mg).

Workup

  1. extractionIt was then extracted with ethyl acetate
  2. washthe obtained organic layer was washed with water and saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd7e803d533142219503b55b9b4e3828
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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