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

HRID 1274997

Reaktionsgleichung

Reaktionsgleichung von HRID 1274997
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 53921131N4,N4-dimethyl-N2-[1-(2-phenylethyl)-4-piperidinyl]-2,4-pyrimidinediamineAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-af6cd92b99fd43cf8bb49c0d311e7a2d
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06159982

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