4,6-Dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidine → HCID 22729401, Verbindung

HRID 2085082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085082
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]([CH3:18])[N:3]=1.[K+].[CH:20]([C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH-:32])(=[O:31])=[O:30])=[N:27][CH:28]=1)([CH3:22])[CH3:21]>CS(C)=O.O>[CH:20]([C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:32][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]([CH3:18])[N:3]=2)(=[O:31])=[O:30])=[N:27][CH:28]=1)([CH3:22])[CH3:21]

Komponenten

5

Edukt 2

HCID 219795994,6-Dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidineHCID 1317209445-Isopropyl pyridine-2-sulfonamide potassium salt

Produkt 1

HCID 22729401HCID 22729401, VerbindungAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2.15 g of 4,6-dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidine in 40 ml of DMSO was added 3.59 g of 5-isopropyl-2-pyridine sulfonamide potassium salt. The mixture was stirred for 72 h at room temperature. The solution was diluted with 350 ml of water and extracted twice with 200 ml of diehtyl ether. The organic layers were extracted twice with water. The combined aqueous layers were acidified to pH 4 with 5 ml of acetic acid and extracted twice with DCM. The organic layers were washed with water, and dried over Na2SO4. The solution was treated with activated charcoal, filtered over Celite and evaporated. The residue was suspended in 30 ml of diethyl ether, filtered off and dried to give 3.15 g of 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide as a pale beige powder. LC-MS: tR=5.18 min, [M+1]+=449.25, [M−1]−=447.31.

Aufarbeitung

  1. extractionextracted twice with 200 ml of diehtyl ether
  2. extractionThe organic layers were extracted twice with water
  3. extractionextracted twice with DCM
  4. washThe organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. additionThe solution was treated with activated charcoal
  7. filtrationfiltered over Celite
  8. customevaporated
  9. filtrationfiltered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-33b8d669455141b1b145455a0e5b113b
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720322B2

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