Sodium borohydride → N-(2-(2-(hydroxymethyl)pyridin-4-yl)-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl)-5-methylpyridine-2-sulfonamide

HRID 1066511

Reaktionsgleichung

Reaktionsgleichung von HRID 1066511
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[N:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])=[C:13]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][N:33]=3)(=[O:31])=[O:30])[N:12]=2)[CH:8]=[CH:7][N:6]=1)=O.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>CCO.C1COCC1>[OH:2][CH2:3][C:5]1[CH:10]=[C:9]([C:11]2[N:12]=[C:13]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][N:33]=3)(=[O:31])=[O:30])[C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])=[C:15]([O:17][CH3:18])[N:16]=2)[CH:8]=[CH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 99588414-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl ester2×

Produkt 1

HCID 9849181N-(2-(2-(hydroxymethyl)pyridin-4-yl)-6-methoxy-5-(2-methoxyphenoxy)pyrimidin-4-yl)-5-methylpyridine-2-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

100 mg of 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl ester, product of example 22, were dissolved in a mixture of EtOH/THF (each 15 ml) on gentle warming and subsequently treated with 42 mg of CaCl2 and 28 mg of NaBH4 at RT. The reaction mixture was stirred at RT for 18 h until which time starting material was consumed according to TLC analysis. The mixture was partitioned between diluted HCl and CH2Cl2. The organic layer was dried over Na2SO4 and the solvent removed in vacuo to give 5-methyl-pyridine-2-sulfonic acid [2-(2-hydroxymethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as a white solid. ISN mass spectrum, m/e 508.3 (M−1 calculated for C24H23N5O6S: 508).

Aufarbeitung

  1. temperatureon gentle warming
  2. customwas consumed
  3. customThe mixture was partitioned between diluted HCl and CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c1198a281f274658b88a2dc46370f9a6
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242601B1

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