Potassium Carbonate → 5-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(1-benzyloxycarbonylpiperidin-3-ylamino)-thiazolo[5,4-d]pyrimidine

HRID 1396726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396726
[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][N:34]([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH2:33]1>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]([NH:31][CH:32]2[CH2:37][CH2:36][CH2:35][N:34]([C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[CH2:33]2)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 17750333Benzyl 3-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)HCID 509418672-(4-Fluorophenethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine

Produkt 1

HCID 469168475-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(1-benzyloxycarbonylpiperidin-3-ylamino)-thiazolo[5,4-d]pyrimidineAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-2-[2-(4-fluorophenyl)ethyl]-7-methanesulfonyl-thiazolo[5,4-d]pyrimidine (50 mg, 0.14 mmol) in 1,4-dioxane (5 ml) was added potassium carbonate (0.42 mmol) and benzyl 3-aminopiperidine-1-carboxylate hydrogen chloride (0.15 mmol). The reaction mixture was stirred at room temperature for 24 hours whereupon the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 1% CH3OH in CH2Cl2), yielding the pure title compound (59 mg) which was characterized by its mass spectrum: MS m/z (%): 507 ([M+H]+, 100).

Aufarbeitung

  1. customwas removed in vacuo
  2. customThe resulting residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio

Quellen und Nachweise

ORD-Eintrag
ord-c803bc7cf80345f08263db40897ff5ee
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901132B2

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