Bromine → 8-Cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1989019

Reaktionsgleichung

Reaktionsgleichung von HRID 1989019
BrBr.[CH2:3]([O:5][C:6]([CH:8]1[CH2:19][N:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[C:9]1=[O:26])=[O:7])[CH3:4].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[C:9](=[O:26])[C:10]2[CH:15]=[N:14][C:13]([S:16][CH3:17])=[N:12][C:11]=2[N:18]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH:19]=1)=[O:7])[CH3:4]

Komponenten

5

Edukt 3

HCID 24408BromineHCID 81531DiisopropylethylamineHCID 68583787HCID 68583787, Verbindung

Produkt 1

HCID 685832078-Cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl esterAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Bromine (0.15 g, 0.94 mmol) was added to a solution of 8-cyclohexyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.28 g, 0.79 mmol) in DCM (10 mL). After 5 min, the solution was concentrated and the crude residue was redissolved in DCM (10 mL) and diisopropylethylamine (0.42 mL, 2.4 mmol) was added. After 15 h, the reaction mixture was partitioned between water and DCM, the organic layer was separated, dried (MgSO4) and concentrated to provide 0.28 g (87%) of the title compound.). Mass Spectrum (LCMS, ESI pos.) Calcd. For C17H21N3O3S: 347.13, found: (M+H) 348.3.

Aufarbeitung

  1. concentrationthe solution was concentrated
  2. dissolutionthe crude residue was redissolved in DCM (10 mL)
  3. waitAfter 15 h
  4. customthe reaction mixture was partitioned between water and DCM
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b55581d20b1647ecaa07731a46ce3aaf
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642270B2

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