tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate

HRID 1617139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617139
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].[Cl:12][C:13]1[C:18](I)=[C:17]([CH3:20])[N:16]=[C:15]([NH2:21])[N:14]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:21][C:15]1[N:14]=[C:13]([Cl:12])[C:18]([C:3]#[C:2][CH2:1][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[C:17]([CH3:20])[N:16]=1

Komponenten

4

Edukt 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Produkt 1

HCID 86633394tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamateAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476HCID 178418476, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

tert-Butyl prop-2-ynylcarbamate (3.11 g), 4-chloro-5-iodo-6-methylpyrimidin-2-amine (1.8 g) and bis(triphenylphosphine)palladium(II) chloride (0.469 g) were combined in TEA (100 mL). The reaction mixture was purged with nitrogen gas for 3 min then copper(I) iodide (0.254 g) added. The resulting mixture was stirred at 70° C. for 16 h, then cooled to rt and filtered. The filtrate was washed with water and brine, dried and the solvents evaporated. The crude material was dissolved in MeOH (20 mL), acidified with acetic acid (1 mL) and purified by SCX and further purified by chromatography eluting 10% MeOH and 0.25% Ammonia (7N) in DCM to afford the subtitle compound 0.93 g.

Aufarbeitung

  1. customThe reaction mixture was purged with nitrogen gas for 3 min
  2. additioncopper(I) iodide (0.254 g) added
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. washThe filtrate was washed with water and brine
  6. customdried
  7. customthe solvents evaporated
  8. dissolutionThe crude material was dissolved in MeOH (20 mL)
  9. custompurified by SCX
  10. customfurther purified by chromatography
  11. washeluting 10% MeOH and 0.25% Ammonia (7N) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-897741a5475f4b26aec29e2304e6a768
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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