4,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidine → 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide

HRID 2085077Notes

Reaction equation

HRID 2085077 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:3]=1.[K+].[CH:25]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([NH-:37])(=[O:36])=[O:35])=[N:32][CH:33]=1)([CH3:27])[CH3:26]>CN(C=O)C>[CH:25]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([NH:37][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:3]=2)(=[O:36])=[O:35])=[N:32][CH:33]=1)([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 111754584,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidineHCID 1317209445-Isopropyl pyridine-2-sulfonamide potassium salt

Product 1

HCID 227294115-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine and 1.43 g of 5-isopropyl pyridine-2-sulfonamide potassium salt were suspended in 20 ml of dry DMF. The mixture was stirred under argon at room temperature and became clear within a few h. After 16 h at room temperature, most of the solvent was removed by evaporation under reduced pressure. The residue was taken up in 20 ml water and the pH was adjusted to 4-5 by adding about 1 ml of acetic acid. A precipitate formed. The precipitate was filtered off, washed with water and dried. The yellow powder was further purified by column chromatography on silica gel eluting first with hexane:ethyl acetate 1:1 then with DCM:MeOH 10:1. 1.43 g of 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide was obtained as a slightly yellow powder. LC-MS: tR=5.00 min, [M+1]+=512.19, [M−1]−=510.26.

Workup

  1. custommost of the solvent was removed by evaporation under reduced pressure
  2. additionby adding about 1 ml of acetic acid
  3. customA precipitate formed
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customThe yellow powder was further purified by column chromatography on silica gel eluting first with hexane:ethyl acetate 1:1

Sources & evidence

ORD record
ord-8b39ebb8050f470d810cbeb76cc59687
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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