1-Propanol, 3-amino-2,2-dimethyl- → 3-{4-[2-(4-Fluorophenyl)-8-isopropoxyimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2,2-dimethylpropan-1-ol

HRID 2233115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233115
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([O:16][CH:17]([CH3:19])[CH3:18])=[N:14][CH:13]=[CH:12][N:11]3[C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23](S(C)(=O)=O)[N:22]=2)=[CH:4][CH:3]=1.[NH2:31][CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([O:16][CH:17]([CH3:19])[CH3:18])=[N:14][CH:13]=[CH:12][N:11]3[C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:31][CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35])[N:22]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 588695382-(4-Fluorophenyl)-8-isopropoxy-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Produkt 1

HCID 160504513-{4-[2-(4-Fluorophenyl)-8-isopropoxyimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2,2-dimethylpropan-1-olAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 2-(4-fluorophenyl)-8-isopropoxy-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine (0.16 g, 0.37 mmol) and 3-amino-2,2-dimethylpropan-1-ol (TCI-US, 0.208 g, 0.74 mmol) in ACN (5 mL) was heated at about 80° C. overnight to give a clear solution. The reaction mixture was cooled to ambient temperature, the volatiles were evaporated, and the resulting residue was dissolved in DCM and washed with water. The organic phase was dried over MgSO4, filtered, and evaporated to give a white solid that was triturated with heptane to afford 0.109 g (64.7%) the title compound as a white solid: LC/MS (Table 1, Method g) Rt=3.01 min; MS m/z: 494.2 (M+H)+.

Aufarbeitung

  1. customto give a clear solution
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe volatiles were evaporated
  4. dissolutionthe resulting residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a white solid
  10. customthat was triturated with heptane

Quellen und Nachweise

ORD-Eintrag
ord-ae0c9fe3293e4b8db6d421c13d94dfb3
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709468B2

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