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Diisopropylethylamine → 7-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl ester

HRID 450119
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 450119
[CH3:1][O:2][C:3](=[O:24])[CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=1[F:16])=O.C(N(C(C)C)CC)(C)C.O(Cl)Cl.[P+5]>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:17]=[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][N:19]2[C:5]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=1[F:16])=[O:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 67234471N-(2-Fluoro-4-methylsulfanyl-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid methyl esterHCID 178479711HCID 178479711, Verbindung

Produkt 1

HCID 672346767-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl esterAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-(2-fluoro-4-methylsulfanyl-phenyl)-2-pyrimidin-4-ylmethyl-malonamic acid methyl ester (2 g, 5.72 mmol) and diisopropylethyl amine (2.9 mL, 17.2 mmol) in dioxane (30 mL) was added phosphorous (V) oxychloride (2.7 mL, 28.6 mmol) and the reaction mixture heated at reflux for 1 hour. The reaction mixture was cooled to 0° C. and quenched with water (10 mL). The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 10-20% ethylacetate in cyclohexane) to yield the title compound as a light brown solid (0.80 g, 42%). LCMS (Method B): RT=3.70 min, M+H+=332.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 hour
  3. customquenched with water (10 mL)
  4. additionThe reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-045306fa0ec2457085b46f4e35388be4
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486963B2

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