Sodium hydride → 2-chloro-N-(2-(isopropylsulfonyl)phenyl)-5-methylpyrimidin-4-amine

HRID 388543

Reaktionsgleichung

Reaktionsgleichung von HRID 388543
[H-].[Na+].[CH:3]([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])(=[O:8])=[O:7])([CH3:5])[CH3:4].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([CH3:24])=[CH:19][N:18]=1>CN(C=O)C.CS(C)=O>[Cl:16][C:17]1[N:22]=[C:21]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6]([CH:3]([CH3:5])[CH3:4])(=[O:8])=[O:7])[C:20]([CH3:24])=[CH:19][N:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 126463662-(Propane-2-sulfonyl)aniline

Produkt 1

HCID 597644732-chloro-N-(2-(isopropylsulfonyl)phenyl)-5-methylpyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3013483N,N-dimethylformamide; methylsulfinylmethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 730 mg of NaH in a mixture of DMF/DMSO (25/2.5 ml) is added drop-wise at 0° C., 2.53 g (12.69 mmol) of 2-(iso-propylsulfonyl)benzenamine in DMF/DMSO (10 ml, ratio 9/1). The solution is stirred 30 minutes at 0° C. and 4.11 g (25.3 mmol, 2 eq.) of 2,4-dichloro-5-methylpyrimidine diluted in 10 ml of DMF/DMSO (ratio: 9/1) is added dropwise. The solution is warmed-up to room temperature and stirred overnight. After work-up, the crude product is directly crystallized from cold CH3CN in several batches to afford 2-chloro-N-(2-(iso-propylsulfonyl)phenyl)-5-methylpyrimidin-4-amine as pale creamy colored crystals: ESMS m/z 326.1 (M+H+).

Aufarbeitung

  1. additionis added drop-wise at 0° C.
  2. additionis added dropwise
  3. temperatureThe solution is warmed-up to room temperature
  4. stirringstirred overnight
  5. customAfter work-up, the crude product is directly crystallized from cold CH3CN in several batches

Quellen und Nachweise

ORD-Eintrag
ord-d7f9c8f2f662470e8b423f3a378c3743
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377921B2

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