alpha-Bromo-o-fluorotoluene → 2-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanol

HRID 1006512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006512
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[NH2:10][C:11]1[S:12][C:13]2[C:18]([NH:19][C@H:20]([CH3:23])[CH2:21][OH:22])=[N:17][C:16]([SH:24])=[N:15][C:14]=2[N:25]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.CN1CCCC1=O>[NH2:10][C:11]1[S:12][C:13]2[C:18]([NH:19][C@H:20]([CH3:23])[CH2:21][OH:22])=[N:17][C:16]([S:24][CH2:4][C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[F:1])=[N:15][C:14]=2[N:25]=1

Komponenten

5

Edukt 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 81531DiisopropylethylamineHCID 178461804HCID 178461804, Verbindung

Produkt 1

HCID 235198222-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanolAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18784345DMSO N-methylpyrrolidinoneLösungsmittel

Versuchsvorschrift

2-fluorobenzylbromide (0.369 g) was added portionwise to a solution of the product of example 32 step b) (0.5 g) and diisopropylethylamine (0.26 g) in DMSO/N-methylpyrrolidinone (4 ml/0.5 ml) at 50° C. and stirring maintained for 1 h. The mixture was partitioned between H2O (200 ml) and EtOAc (120 ml). The organics were recovered and washed flier with H2O (200 ml), dried over MgSO4 and concentrated onto silica gel. The subtitle compound was purified by flash chromatography using DCM then EtOAc as eluents to yield a white solid (245 mg, 35%).

Aufarbeitung

  1. temperaturemaintained for 1 h
  2. customThe mixture was partitioned between H2O (200 ml) and EtOAc (120 ml)
  3. customThe organics were recovered
  4. washwashed flier with H2O (200 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated onto silica gel
  7. customThe subtitle compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bcd0ebf3d84c48b8862abb3994de21c2
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790850B1

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