Diisopropylethylamine → N-{3-[(2,5-dichloro-pyrimidin-4-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulphonamide

HRID 1255413

Reaktionsgleichung

Reaktionsgleichung von HRID 1255413
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][CH2:11][C:12]1[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH2:11][C:12]2[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 45480403N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide

Produkt 1

HCID 86648149N-{3-[(2,5-dichloro-pyrimidin-4-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulphonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,4,5-trichloropyrimidine (1.0 g, 5.45 mmol) is suspended in 20 mL DCM and the reaction mixture is cooled to 0° C. Then a solution of N-(3-aminomethyl-pyridin-2-yl)-N-methyl-methanesulphonamide (1.17 g, 5.45 mmol) and DIPEA (1.95 mL, 10.9 mmol) in 10 mL DCM is added and the mixture is stirred overnight. The reaction mixture is diluted with DCM and washed 3× with 1 N NH4Cl solution. The organic phase is dried on magnesium sulphate and evaporated down in vacuo. The crude product A-2b (HPLC-MS: tRet.=2.00 min; MS (M+H)+=362) is used in successive reactions without further purification.

Aufarbeitung

  1. washwashed 3× with 1 N NH4Cl solution
  2. customThe organic phase is dried on magnesium sulphate
  3. customevaporated down in vacuo
  4. customThe crude product A-2b (HPLC-MS: tRet.=2.00 min; MS (M+H)+=362) is used in successive reactions without further purification

Quellen und Nachweise

ORD-Eintrag
ord-384e284fd506437fad52d670dca5853c
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461147B2

Verknüpfte Notizen

Wird geladen…