3-Pentanamine → 5-bromo-2-chloro-N-(pentan-3-yl)pyrimidin-4-amine

HRID 2189286Notes

Reaction equation

HRID 2189286 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:10]([CH:12]([NH2:15])[CH2:13][CH3:14])[CH3:11].C(N(CC)C(C)C)(C)C>C(O)C>[Br:1][C:2]1[C:3]([NH:15][CH:12]([CH2:13][CH3:14])[CH2:10][CH3:11])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 120193-PentanamineHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 580158915-bromo-2-chloro-N-(pentan-3-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (4.56 g, 20 mmol) in ethanol (9 mL) is added 1-ethylpropylamine (2.6 mL, 22 mmol) and N,N-diisopropylethylamine (7 mL, 40 mmol) at ambient temperature. The reaction mixture is stirred at ambient temperature for 16 h and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/hexane 3:97 to 30:70) to give (5-bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine. LCMS: 280 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by flash chromatography (SiO2, EtOAc/hexane 3:97 to 30:70)

Sources & evidence

ORD record
ord-6be90e367e174784824b6796f9d46164
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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