Water → 2-((4-(1-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1091690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091690
[CH3:1][C:2]1[S:23][C:5]2[N:6]=[C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH:17]=[O:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)[NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[CH3:24][Mg]Br.O>C(OCC)C>[OH:18][CH:17]([C:15]1[C:14]([C:19]([F:21])([F:22])[F:20])=[N:13][N:12]([CH2:11][C:7]2[NH:8][C:9](=[O:10])[C:4]3[CH:3]=[C:2]([CH3:1])[S:23][C:5]=3[N:6]=2)[CH:16]=1)[CH3:24]

Komponenten

5

Edukt 3

HCID 962WaterHCID 866303971-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 665918052-((4-(1-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (100 mg, 0.292 mmol) was dissolved in diethyl ether (10 mL) and cooled to −78° C. with a dry ice/acetone bath. The reaction was performed under a nitrogen atmosphere. Methylmagnesium bromide (35 mg, 0.292 mmol) was added dropwise and the reaction mixture allowed to warm to RT and stirred for 2 h. Water was added and the reaction mixture extracted into EtOAc (×3). The combined EtOAc layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by preparative reverse phase HPLC gave the title product (8 mg, 0.023 mmol, 8%).

Aufarbeitung

  1. temperatureto warm to RT
  2. extractionthe reaction mixture extracted into EtOAc (×3)
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-477d5538e33c47bd923822508605b38c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129397B2

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