3-(Piperidinosulfonyl)aniline → 5-Methyl-N2-[3-(piperidine-1-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

HRID 1097089

Reaktionsgleichung

Reaktionsgleichung von HRID 1097089
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[N:10]1([S:16]([C:19]2[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)(=O)C>[CH3:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([S:16]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)(=[O:18])=[O:17])[CH:20]=2)=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 27947913-(Piperidinosulfonyl)anilineHCID 43021752-Chloro-5-methylpyrimidin-4-amine

Produkt 1

HCID 576750845-Methyl-N2-[3-(piperidine-1-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.25 g, 1.74 mmol) and 3-(piperidine-1-sulfonyl)-phenylamine (0.50 g, 2.1 mmol) in acetic acid (4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 130° C. for 15 min. After cooling to room temperature, the cap was removed and the mixture concentrated. The residue was taken in water (20 mL) and pH adjusted to ˜9 with 10% NaOH solution. The resulting solution was extracted with EtOAc (2×30 mL) and the organic layer separated. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the crude product (˜0.6 g) used in the next step without purification. MS (ES+): m/z 348 (M+H)+.

Aufarbeitung

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 130° C. for 15 min
  3. customthe cap was removed
  4. concentrationthe mixture concentrated
  5. extractionThe resulting solution was extracted with EtOAc (2×30 mL)
  6. customthe organic layer separated
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customthe crude product (˜0.6 g) used in the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-901037a82ea44112850b231a9a96ff2f
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138199B2

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