Pyridine → [2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl acetate

HRID 1508715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508715
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([CH2:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:10]=2)=[CH:4][C:3]=1[CH2:24][OH:25].[C:26](Cl)(=[O:28])[CH3:27].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[C:26]([O:25][CH2:24][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[C:14]([CH2:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:10]=2)[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:28])[CH3:27]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 90112603[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol

Produkt 1

HCID 90113035[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl acetateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A 18-mL vial was charged with [2-bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol (93 mg, 0.21 mmol), acetyl chloride (100 mg, 1.27 mmol, 6 eq.). Pyridine (1 ml) was added followed by 4-(dimethylamino)pyridine (5 mg, 0.2 eq.). The resulting mixture was stirred at rt for 2 hr. Then water was (5 ml) added. The precipitate was collected and washed with water. The crude product was purified by chromatography on silica gel using dichloromethane as eluent to give the tile compound (73 mg, 72% yield).

Aufarbeitung

  1. additionadded
  2. customThe precipitate was collected
  3. washwashed with water
  4. customThe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4ef87933092a457e89f43f5a0fb30ce4
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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