Water → N-benzyl-6-chloropyrimidin-4-amine

HRID 58162Notes

Reaction equation

HRID 58162 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CC(O)C>[CH2:18]([NH:25][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 3771857N-benzyl-6-chloropyrimidin-4-amineYield 68.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-pyrimidine (1.5 g, 10 mmol) in iPrOH (40 mL) and DIPEA (1.55 g, 12 mmol) was added a solution of benzylamine (1.28 g, 12 mmol) at room temperature. The resulting mixture was stirred at room temperature for 2.5 hours. Water was added and the mixture was extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated to give the crude product, which was purified by flash chromatography on silica to obtain the title compound (1.5 g, yield: 68%) as a white solid. H NMR (300 MHz, CDCl3) δ 8.35 (br s, 1H), 7.20-7.38 (m, 5H), 6.35 (s, 1H), 4.52 (s, 2H); MS (ESI): 220 [M+H]+.

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-bd7eb2ddea574471a3c85b558ca28f0c
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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