Phenyl chloroformate → phenyl (4-{4-[1-methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)carbamate

HRID 2353671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353671
[CH3:1][C:2]([C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]2[CH3:20])[N:11]=[C:10]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[N:9]=1)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].C(=O)(O)[O-].[Na+].Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>O1CCOCC1>[CH3:1][C:2]([C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]2[CH3:20])[N:11]=[C:10]([C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:34](=[O:35])[O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:25][CH:26]=2)[N:9]=1)([S:4]([CH3:7])(=[O:5])=[O:6])[CH3:3]

Komponenten

5

Edukt 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 59380004(4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)amine

Produkt 1

HCID 59379977phenyl (4-{4-[1-methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)carbamateAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)amine (3.6 g, 8.77 mmol) was dissolved in dioxane (20 mL). Sodium bicarbonate (1.1 g, 13.15 mmol) was added, followed by phenyl chloroformate (1.1 mL, 8.77 mmol) and the reaction stirred at room temperature for 2 hours. The solvent was removed in vacuo, and the resultant oil partitioned between 20 mL DCM and 20 mL water. The organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. The cream solid obtained was chromatographed on silica, eluting with 0-50% ethyl acetate in DCM, to give the desired material as a white solid (2 g).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe resultant oil partitioned between 20 mL DCM and 20 mL water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe cream solid obtained
  7. customwas chromatographed on silica
  8. washeluting with 0-50% ethyl acetate in DCM

Quellen und Nachweise

ORD-Eintrag
ord-6d079e106e9140ee8c90bd71297716f9
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750003B2

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