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

HRID 58165Notes

Reaction equation

HRID 58165 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][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.O>CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:25][CH2:24][C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 709434,6-DichloropyrimidineHCID 773174-PyridinemethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 467414356-Chloro-N-(4-pyridinylmethyl)-4-pyrimidinamineYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4,6-dichloro-pyrimidine (1.5 g, 10.5 mmol) and DIPEA (1.62 g, 12.6 mmol) in iPrOH (40 mL) was added 4-pyridinylmethanamine (1.2 g, 11 mmol) at room temperature. The resulting mixture was stirred at room temperature for 2 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 (1.8 g, yield: 80%). 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 Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-0de69dd0b4484ea0ae8917cc1901149a
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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