Sodium Carbonate → tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

HRID 527413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527413
[CH2:1]([C:3]1[C:14](=[O:15])[N:13]([C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=2)[C:6]2[N:7]=[C:8]([S:11][CH3:12])[N:9]=[CH:10][C:5]=2[CH:4]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:35].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([C:3]1[C:14](=[O:15])[N:13]([C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=2)[C:6]2[N:7]=[C:8]([S:11]([CH3:12])=[O:35])[N:9]=[CH:10][C:5]=2[CH:4]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 86732011tert-butyl (3-(6-ethyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

Produkt 1

HCID 86732026tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

At 0° C., a suspension of tert-butyl (3-(6-ethyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (55) (720 mg, 1.75 mmol) in DCM (15 mL) was treated with 3-chloroperoxybenzoic acid (70 wt. %, 460 mg, 1.87 mmol) in one portion and stirred at 0° C. for 1 h. The reaction mixture was diluted with DCM (15 mL), and treated with ice and a 10% solution of Na2CO3 (ca. 10 mL). The DCM layer was separated and the aqueous layer was extracted with an additional amount of DCM (2×50 mL), dried over sodium sulfate and concentrated to give tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (6a) (682 mg, 1.59 mmol, 91% yield) as a light yellow amorphous solid. m/z (ESI, +ve ion) 451.0 (M+Na)+. The crude material was used in the subsequent step without further purification.

Aufarbeitung

  1. additiontreated with ice
  2. customThe DCM layer was separated
  3. extractionthe aqueous layer was extracted with an additional amount of DCM (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f0bacf24056c4ac28762ba30a734c8fe
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346801B2

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