Triethylamine → 6-chloro-5-fluoro-N-methyl-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

HRID 1366630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366630
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][NH:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1.C(N(CC)CC)C>C1COCC1.O>[Cl:9][C:6]1[N:5]=[C:4]([S:10][CH3:11])[N:3]=[C:2]([N:13]([CH3:12])[CH2:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[C:7]=1[F:8]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 18939834Methyl((1,3-thiazol-2-yl)methyl)amineHCID 223782774,6-Dichloro-5-fluoro-2-(methylsulfanyl)pyrimidine2×

Produkt 1

HCID 866370126-chloro-5-fluoro-N-methyl-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamineAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4,6-Dichloro-5-fluoro-2-(methylthio)pyrimidine (see Intermediate E) (0.3313 g, 1.563 mmol), N-methyl-1-(1,3-thiazol-2-yl)methanamine (0.200 g, 1.5625 mmol), and triethylamine (0.26 mL, 1.8654 mmol) were dissolved in THF (5 mL) and left to stir overnight. Then the reaction mixture was diluted with water and the aqueous layer was extracted with ethyl acetate. The organics were dried (Na2SO4) and concentrated to produce 6-chloro-5-fluoro-N-methyl-2-(methylthio)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine as a yellow oil (0.4928 g). LCMS: (M+H)+=305.0.

Aufarbeitung

  1. waitleft
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8c5319affb4c4176b91bd5048b8cbab3
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

Notizen zur Reaktion

Wird geladen…