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Diisopropylethylamine → 4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 2280750
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2280750
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.Cl.[NH2:13][C@H:14]1[CH2:19][C@@H:18]([OH:20])[C@H:17]([CH3:21])[CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>CN(C=O)C>[OH:20][C@H:18]1[C@H:17]([CH3:21])[CH2:16][CH2:15][C@@H:14]([NH:13][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)[CH2:19]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 86676342(1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride

Produkt 1

HCID 712372574-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-2-(methylthio)pyrimidine-5-carbonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirring solution of 4-chloro-2-(methylthio)-pyrimidine-5-carbonitrile (310 mg, 1.670 mmol) and (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride (304 mg, 1.837 mmol; synthesis described herein) in DMF (2.4 mL) was added DIEA (0.873 ml. 5.01 mmol). The resulting mixture was stirred at 60° C. for 2 h. LCMS showed the reaction to be complete. The solvent was evaporated under reduced pressure and the residue diluted with 150 mL ethyl acetate and 50 mL water. The layers were separated and the aqueous phase was extracted with 75 mL ethyl acetate. The combined ethyl acetate layers were washed with brine (2×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to an oil that solidified upon standing to afford 4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-2-(methylthio)pyrimidine-5-carbonitrile (418 mg, 1.503 mmol, 90% yield). MS (ESI) m/z 279.3 [M+1]+.

Aufarbeitung

  1. customsynthesis
  2. customthe reaction
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue diluted with 150 mL ethyl acetate and 50 mL water
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with 75 mL ethyl acetate
  7. washThe combined ethyl acetate layers were washed with brine (2×50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil that

Quellen und Nachweise

ORD-Eintrag
ord-5d65df42823c4aed9ee937cf25a0aaa6
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09139534B2

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