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

HRID 1066495

Reaction equation

HRID 1066495 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)(=[O:24])=[O:23])[C:18]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])=[C:17]([O:41][CH3:42])[N:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C(O)C.C1CCC=CC=1>O1CCOCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)(=[O:24])=[O:23])[C:18]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])=[C:17]([O:41][CH3:42])[N:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 116051,3-CyclohexadieneHCID 538017195-Methyl-pyridine-2-sulfonic acid [2-(3-benzyloxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Product 1

HCID 98485845-Methyl-pyridine-2-sulfonic acid [2-(3-hydroxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

1.46 g of 5-methyl-pyridine-2-sulfonic acid [2-(3-benzyloxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide were dissolved in dioxane (25 ml) by gentle warming than ethanol (50 ml) was added followed by cyclohexadiene (6 g) and palladium on charcoal, 10%, (1.46 g). The solution was refluxed for 20 h, the catalyst removed by filtration and the solution concentrated on a rotary evaporator. The yellow crystalline solid that precipitated was collected, washed with ether and dried in a vacuum to give the desired 5-methyl-pyridine-2-sulfonic acid [2-(3-hydroxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as off-white crystals. ISP mass spectrum, m/e 495.2 (M+1 calculated for C24H22N4O6S1: 495). Melting point 211°-216° C.

Workup

  1. additionwas added
  2. temperatureThe solution was refluxed for 20 h
  3. customthe catalyst removed by filtration
  4. concentrationthe solution concentrated on a rotary evaporator
  5. customThe yellow crystalline solid that precipitated
  6. customwas collected
  7. washwashed with ether
  8. customdried in a vacuum

Sources & evidence

ORD record
ord-d4d00f622d1a4fadaad775f5f73fa339
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Linked notes

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