Water → 6-Chloro-N-(2-pyridinylmethyl)-4-pyrimidinamine

HRID 58164Notes

Reaction equation

HRID 58164 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.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][NH2:25].O>CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 195092-PyridinemethanamineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 534102726-Chloro-N-(2-pyridinylmethyl)-4-pyrimidinamineYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-pyrimidine (1 g, 7 mmol) in iPrOH (40 mL) and DIPEA (1.16 g, 9 mmol) was added a solution of 2-pyridinylmethanamine (970 g, 9 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 sodium sulfate and concentrated to give a crude product, which was purified by flash chromatography on silica to obtain the title compound (1.2 g, yield: 78%). MS (ESI): 221 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-fc5e87935fb649a98361c1c74cfdadd2
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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