Tetrahydrofuran → 1-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone

HRID 2069468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069468
CON(C)[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([NH:13][CH:14]([CH3:16])[CH3:15])[N:7]=1)=[O:5].[CH2:18]1COCC1>C[Mg]Br.CCOCC>[CH:14]([NH:13][C:8]1[N:7]=[C:6]([C:4](=[O:5])[CH3:18])[CH:11]=[C:10]([CH3:12])[N:9]=1)([CH3:15])[CH3:16]

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 866453112-Isopropylamino-6-methyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide

Produkt 1

HCID 685106621-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 178418573HCID 178418573, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide (2.39 g, 10.0 mmol) in THF (50 mL), methyl magnesium bromide (7.0 mL of a 3 M solution in ether, 20.1 mmol) is added dropwise at 5° C. The mixture is stirred at 5° C. for 1.5 h. The reaction is quenched by adding NH4Cl. The mixture is diluted with EtOAc (75 mL), washed with sat. aq. NaHCO3, dried over Na2SO4, filtered and concentrated to give 1-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone (1.71 g) as a yellow solid. LC-MS: tR=0.75 min, [M+H]+=194.01; 1H NMR (CDCl3): δ 1.29 (d, J=6.5 Hz, 6H), 2.41 (s, 3H), 2.62 (s, 3H), 4.22 (m, 1H), 5.02 (m, 1H), 6.97 (s, 1H).

Aufarbeitung

  1. customThe reaction is quenched
  2. additionby adding NH4Cl
  3. additionThe mixture is diluted with EtOAc (75 mL)
  4. washwashed with sat. aq. NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6bc4ff87e12b43aa97e52f9ab50c5571
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299086B2

Notizen zur Reaktion

Wird geladen…