Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate → (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 599323

Reaktionsgleichung

Reaktionsgleichung von HRID 599323
[CH3:1][NH:2][C:3]1[C:8]([C:9](OCC)=[O:10])=[CH:7][N:6]=[C:5]([S:14][CH3:15])[N:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[C:5]([S:14][CH3:15])[N:4]=1

Komponenten

4

Edukt 2

HCID 295697Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10679092(4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(methylamino)-2-(methylthio)pyrimidine-5-carboxylate (30 g, 132 mmol) in THF (300 mL) was added LiAlH4 (7.5 g, 198 mmol). The reaction mixture was stirred for 1 h at RT. The reaction was carefully quenched with 10 mL water, 7 mL of 10% aq NaOH. The mixture was stirred for 1 h, filtered and the filtrate was concentrated to give (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (22.0 g, 90% yield). 1H NMR (300 MHz, DMSO-d6): 7.79 (s, 1 H), 6.79 (m, 1 H), 5.04 (t, J=5.4 Hz, 1 H), 4.27 (d, J=5.4 Hz, 2H), 2.83 (d, J=4.8 Hz, 3 H), 2.40 (s, 3 H). MS (ESI) m/z: 186.1 (M+H+).

Aufarbeitung

  1. customThe reaction was carefully quenched with 10 mL water, 7 mL of 10% aq NaOH
  2. stirringThe mixture was stirred for 1 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e94ccc15e0fb4ab2b314205efbf8ec01
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897762B2

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