2-Chloro-N,N-dimethylpyrimidin-4-amine → N4,N4-dimethyl-N2-[1-(2-phenylethyl)-4-piperidinyl]-2,4-pyrimidinediamine

HRID 1937416

Reaction equation

HRID 1937416 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:17]1[N:22]=[C:21]([N:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][N:18]=1>O>[CH3:24][N:23]([CH3:25])[C:21]1[CH:20]=[CH:19][N:18]=[C:17]([NH:15][CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11]2)[N:22]=1

Participants

4

Reactant 2

HCID 959752-Chloro-N,N-dimethylpyrimidin-4-amineHCID 107287881-(2-Phenylethyl)piperidin-4-amine

Product 1

HCID 53921131N4,N4-dimethyl-N2-[1-(2-phenylethyl)-4-piperidinyl]-2,4-pyrimidinediamineYield 28.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(2-phenylethyl)-4-piperidinamine (8.17 g) and 2-chloro-N,N-dimethyl-4-pyrimidinamine (6.3 g) was stirred for 20 hours at 120° C. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic layer was washed with water, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH(NH3) 96/4). The pure fractions were collected and the solvent evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 3.69 g (28.4%) of N4,N4-dimethyl-N2-[1-(2-phenylethyl)-4-piperidinyl]-2,4-pyrimidinediamine (comp. 11).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH(NH3) 96/4)
  7. customThe pure fractions were collected
  8. customthe solvent evaporated
  9. customThe residue was crystallized from CH3CN
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-58cd85450cae421b8d8e48d75748ed99
Source dataset
uspto-grants-2002_05
Patent number
US06395742B1

Linked notes

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