Benzyl Chloride → 5-Methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride

HRID 1066513

Reaktionsgleichung

Reaktionsgleichung von HRID 1066513
[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:18])=[O:17])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:11]([O:35][CH3:36])[N:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].C([Cl:44])C1C=CC=CC=1>CO.[Pd]>[ClH:44].[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:18])=[O:17])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:11]([O:35][CH3:36])[N:10]=2)[CH:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 2

HCID 7503Benzyl ChlorideHCID 99358945-Methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Produkt 1

HCID 867569945-Methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 100 mg of 5-methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide, product of example 19, dissolved in MeOH (5 ml), was treated with 47.5 mg of benzyl chloride, 10 mg of palladium on charcoal (10%) and then hydrogenated at RT for hours until TLC analysis indicated completion of transformation. The catalyst was filtered off, and the solution concentrated in vacuo. The crystalline solid that precipitated was collected by filtration, washed with ether and dried in a high vacuum to give 5-methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride as light yellow crystals. ISP mass spectrum, m/e 509.3 (M+1 calculated for C24H24N6O5S: 509).

Aufarbeitung

  1. waithydrogenated at RT for hours until TLC analysis
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solution concentrated in vacuo
  4. customThe crystalline solid that precipitated
  5. filtrationwas collected by filtration
  6. washwashed with ether
  7. customdried in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-587b358c8d2f457da7e3776437dc0fe4
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242601B1

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