Water → [5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](phenyl)methanol

HRID 32615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32615
CN(C)C(=O)[O:4][CH:5]([C:12]1[N:13]([CH3:33])[C:14]([C:23]2[S:24][C:25]3[N:26]=[CH:27][N:28]=[C:29]([NH2:32])[C:30]=3[N:31]=2)=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(C(F)(F)F)=O.O>C1COCC1.CCOC(C)=O>[NH2:32][C:29]1[C:30]2[N:31]=[C:23]([C:14]3[N:13]([CH3:33])[C:12]([CH:5]([C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)[OH:4])=[N:16][C:15]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:24][C:25]=2[N:26]=[CH:27][N:28]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 69197371[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](phenyl)methyl dimethylcarbamate2×

Produkt 1

HCID 17965801[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](phenyl)methanolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

[5-(7-Amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl](phenyl)methyl dimethylcarbamate (Intermediate 97) (25 mg) was dissolved in THF (4 mL), TFA (0.1 mL) and water (0.1 mL) added then heated at reflux under an inert atmosphere. After 2 hours, cooled to ambient temperature, diluted with EtOAc (10 mL), washed with saturated aqueous NaHCO3 (10 mL), organic layer dried (MgSO4), filtered and concentrated in vacuo. Residue was purified by flash chromatography on silica eluting with 4% MeOH/DCM to give the title compound as a colourless foam (21 mg, 99%);

Aufarbeitung

  1. temperaturethen heated
  2. temperatureat reflux under an inert atmosphere
  3. washwashed with saturated aqueous NaHCO3 (10 mL), organic layer
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customResidue was purified by flash chromatography on silica eluting with 4% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-a3c5e273aecc40309ddc9f7091ed22c4
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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