Sodium borohydride → 5-Methyl-pyridine-2-sulfonic acid [2-[3-(2-hydroxy-ethoxy)-phenyl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

HRID 1066502Notes

Reaction equation

HRID 1066502 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[C:14]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][N:34]=3)(=[O:32])=[O:31])[N:13]=2)[CH:7]=1.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>CCO.C1COCC1>[OH:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[N:13]=[C:14]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][N:34]=3)(=[O:31])=[O:32])[C:15]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[C:16]([O:18][CH3:19])[N:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 53666334{3-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenoxy}-acetic acid methyl ester2×

Product 1

HCID 98719405-Methyl-pyridine-2-sulfonic acid [2-[3-(2-hydroxy-ethoxy)-phenyl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

70 mg of {3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenoxy}-acetic acid methyl ester, product of example 2, were dissolved in a mixture of EtOH/THF (each 3 ml) on gentle warming and subsequently treated with 27.4 mg of CaCl2 and 18.7 mg of NaBH4 at RT. The reaction mixture was stirred at RT for 1.5 h until which time starting material was consumed according to TLC analysis (CH2Cl2/EtOAc: 3/1). The mixture was partitioned between 10% citric acid and EtOAc. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2EtOAc: 3/1). Combination of the purified fractions and evacuation in vacuo afforded 5-methyl-pyridine-2-sulfonic acid [2-[3-(2-hydroxy-ethoxy)-phenyl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as a white solid. ISP mass spectrum, m/e 539.3 (M+1 calculated for C26H26N4O7S: 539).

Workup

  1. temperatureon gentle warming
  2. customwas consumed
  3. customThe mixture was partitioned between 10% citric acid and EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe residue was purified on a silica gel chromatography column (eluted with Me2Cl2EtOAc: 3/1)

Sources & evidence

ORD record
ord-84924afc09cf42e69ac325458144d14a
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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