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Potassium Carbonate → HCID 86633877, Verbindung

HRID 1687121
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1687121
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[OH:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1>O1CCCC1>[Cl:16][C:17]1[N:22]=[C:21]([NH:2][C@@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]2[OH:9])[C:20]([Cl:24])=[CH:19][N:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Produkt 1

HCID 86633877HCID 86633877, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrahydrofuran (100 mL) was added to racemic trans-2-amino-cyclohexanol hydrochloride (4.28 g, 28.2 mmol) and potassium carbonate (12.1 g, 88 mmol). The mixture was cooled at 0° C. before 2,4,5-trichloropyrimidine (2 mL, 17.4 mmol) was added. After 3 hours, the mixture was partitioned between water and ethyl acetate, the aq. layer was extracted and the combined extracts were dried and conc. in vacuo. The crude product was taken up in ethyl acetate and washed with 10% w/v citric acid, then with sodium bicarbonate, dried over sodium sulfate and conc. in vacuo to give rel-(1R,2R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclohexanol (2.27 g, 50%) as a white solid. m.p.=139-142° C.; LCMS (m/e) 262 (M+1); 1H-NMR (DMSO-d6, 400 MHz) δ 8.12 (s, 1H), 7.45 (m, 1H), 68 (m, 1H), 3.81 (m, 1H), 3.55 (m, 1H), 1.92 (m, 1H), 1.81 (m, 1H), 1.67 (m, 2H), 1.41 (m, 1H), 1.26 (m, 3H).

Aufarbeitung

  1. additionwas added
  2. customthe mixture was partitioned between water and ethyl acetate
  3. extractionthe aq. layer was extracted
  4. customthe combined extracts were dried and conc. in vacuo
  5. washwashed with 10% w/v citric acid
  6. dry with materialwith sodium bicarbonate, dried over sodium sulfate and conc. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3eafe032239b4631a56031c688e3e1a6
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08148391B2

Notizen zur Reaktion

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