Triethylamine → N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(4-pyrimidinyl)urea

HRID 2182047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182047
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12](C(O)=O)[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1.C([N:19]([CH2:22][CH3:23])[CH2:20]C)C.[NH2:24][C:25]1C=C[N:28]=[CH:27][N:26]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12]([NH:24][C:25]([NH:26][C:27]4[CH:23]=[CH:22][N:19]=[CH:20][N:28]=4)=[O:38])[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 689584-AminopyrimidineHCID 199401P,P-Diphenylphosphinic azideHCID 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid

Produkt 1

HCID 60077559N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(4-pyrimidinyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid (50 mg, 0.22 mmol, ee ˜90%) was mixed with toluene (1 ml), triethylamine (0.034 ml, 1.1 eq), 4-aminopyrimidine (25 mg, 1.1 eq), DPPA (0.054 ml, 1.1 eq). The reaction mixture was then heated with stirring at 110° C. for 3 h. The reaction mixture was concentrated by rotary evaporation and the product was crystallized from ethanol and collected by filtration to give 20 mg of the product as white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. concentrationThe reaction mixture was concentrated by rotary evaporation
  3. customthe product was crystallized from ethanol
  4. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-34c05ac89f0a4bbe86158a2e9d76bcf8
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894177B2

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