Aluminium lithium hydride → HCID 59614410, Verbindung

HRID 409455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409455
C[O:2][C:3]([C:5]1[C:6]([N:17]2[CH2:21][C@@H:20]([N:22]([CH2:35][C:36]3[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=3)[C:23]3[N:28]=[CH:27][C:26]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)=[CH:25][N:24]=3)[CH2:19][C@H:18]2[CH2:50][CH3:51])=[N:7][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:9][CH:10]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:48][C:46]([F:47])([F:49])[C:38]1[CH:37]=[C:36]([CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=1)[CH2:35][N:22]([C:23]1[N:28]=[CH:27][C:26]([C:29]2[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=2)=[CH:25][N:24]=1)[C@@H:20]1[CH2:21][N:17]([C:6]2[C:5]([CH2:3][OH:2])=[CH:10][N:9]=[C:8]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[N:7]=2)[C@H:18]([CH2:50][CH3:51])[CH2:19]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 59614359HCID 59614359, Verbindung

Produkt 1

HCID 59614410HCID 59614410, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidine-5-carboxylic acid methyl ester (250 mg, 0.33 mmol) in 1.5 mL of THF is added LAH (24 mg, 0.66 mmol). After stirred at room temperature for 3.5 hours, the reaction is quenched by Glauber's salt. The mixture is filtered on celite, and the filtrate is concentrated. The obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc) to give [4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidin-5-yl]-methanol (40 mg, 20% yields); ESI-MS m/z: 690 [M+1]+, Retention time 5.79 min (condition B).

Aufarbeitung

  1. customthe reaction is quenched by Glauber's salt
  2. filtrationThe mixture is filtered on celite
  3. concentrationthe filtrate is concentrated
  4. customThe obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c704939dcca04982be8c855f3ff912cc
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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