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

HRID 1066511Notes

Reaction equation

HRID 1066511 reaction equation
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

Participants

5

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c1198a281f274658b88a2dc46370f9a6
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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