N-bromobutanimide → 5-Bromo-4-(1-methylethyl)-2-pyrimidinamine

HRID 1875915Notes

Reaction equation

HRID 1875915 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]([C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[N:13]=1)([CH3:11])[CH3:10]>C(Cl)(Cl)Cl>[Br:1][C:17]1[C:12]([CH:9]([CH3:11])[CH3:10])=[N:13][C:14]([NH2:18])=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 146392414-(Propan-2-yl)pyrimidin-2-amine

Product 1

HCID 534184355-Bromo-4-(1-methylethyl)-2-pyrimidinamineYield 113.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (0.5 g, 2.8 mmol) was added to a solution of 4-isopropylpyrimidin-2-amine (0.39 g, 2.81 mmol) in chloroform. The resultant yellow solution was stirred at ambient temperature for 1 h and concentrated in vacuo. The residue was purified by column chromatography (3-10% 9:1 methanol:ammonium hydroxide in chloroform) to afford 5-bromo-4-isopropylpyrimidin-2-amine (0.69 g, 3.18 mmol, 113%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.21 (1H, s), 6.75 (2H, s), 3.10-3.23 (1H, m), 1.14 (6H, d, J=6.80 Hz). MS (LC/MS) R.T.=2.58; [M]+=216.09.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (3-10% 9:1 methanol:ammonium hydroxide in chloroform)

Sources & evidence

ORD record
ord-e66cabcabd284aa084b928003f27a520
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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