Hydrochloric Acid → HCID 178441874, Verbindung

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:10]([C:26]([O:28]C(C)(C)C)=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O.O>[CH2:1]([O:8][C:9]1[C:10]([C:26]([OH:28])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:18])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:25])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

tert-Butyl 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylate (55) (260 mg, 598 μmol, Eq: 1.00) was stirred in tetrahydrofuran/water. Lithium hydroxide monohydrate (126 mg, 2.99 mmol, Eq: 5) was added. The reaction mixture was heated at 85° C. for 7 hours, cooled, and stirred at room temperature for 16 hours. 1N HCl was added until precipitate forms (about 10 ml). The mixture was diluted with water, extracted three times with ethyl acetate, washed with brine and dried over magnesium sulfate. The solvent was removed on a rotary evaporator to give 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylic acid (56) as a white solid (155 mg, 68%).

Aufarbeitung

temperaturecooled
extractionextracted three times with ethyl acetate
washwashed with brine
dry with materialdried over magnesium sulfate
customThe solvent was removed on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag: ord-3cc2b77cf4814f0bb49373b7f1bc6b06
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09045486B2

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