Hydrochloric Acid → 2-Dimethylamino-5-pyrimidinylboric acid hydrochloride

HRID 492120Notes

Reaction equation

HRID 492120 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.C([Li])CCC.[B:16]([O:25]C(C)C)([O:21]C(C)C)[O:17]C(C)C.[ClH:29]>C1COCC1>[ClH:29].[CH3:9][N:8]([CH3:10])[C:5]1[N:4]=[CH:3][C:2]([O:17][B:16]([OH:25])[OH:21])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 127353155-Bromo-N,N-dimethylpyrimidin-2-amineHCID 178418339Butyllithium

Product 1

HCID 688198552-Dimethylamino-5-pyrimidinylboric acid hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-bromo-2-dimethylaminopyrimidine (2.0 g, 9.9 mmol: Bull. Chem. Soc. Jpn., 72, 2523 (1999)) dissolved in THF (25 ml) was added 1.56 M of n-butyl lithium (hexane solution, 7.0 ml, 10.9 mmol) under cooling with a dry ice-acetone bath. After stirring the mixture for 40 minutes, a solution of triisopropyl borate (3.5 ml, 0.15 ml) dissolved in THF (6 ml) was added to the reaction mixture. The temperature of the mixture was raised to room temperature, hydrochloric acid was added to the mixture, and then the solvent was removed. The residue was triturated by methanol-diethyl ether to give 2-dimethylamino-5-pyrimidinylboric acid hydrochloride (2.26 g).

Workup

  1. temperatureunder cooling with a dry ice-acetone bath
  2. additionwas added to the reaction mixture
  3. customthe solvent was removed
  4. customThe residue was triturated by methanol-diethyl ether

Sources & evidence

ORD record
ord-b4d2862d954f4ccbbc3a6266cd228b4b
Source dataset
uspto-grants-2009_05
Patent number
US07531655B2

Reaction notes

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