Phosphorus oxychloride → (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 81005

Reaktionsgleichung

Reaktionsgleichung von HRID 81005
[CH3:1][C@H:2]1[C:10]2[C:9](O)=[N:8][CH:7]=[N:6][C:5]=2[CH2:4][CH2:3]1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:9]1[C:10]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]=2[N:6]=[CH:7][N:8]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178461168HCID 178461168, Verbindung

Produkt 1

HCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineAusbeute 49 %

Versuchsvorschrift

A mixture of (R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (5.8 g, 38.62 mmol) in POCl3 (20 mL) was refluxed for 5 minutes. The excess POCl3 was removed under vacuum, and the residue was dissolved in DCM (50 mL). The mixture was then added to saturated NaHCO3 (200 mL). The aqueous phase was extracted with DCM (3×100 mL), and the combined organic phases were dried and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate to give (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (3.18 g, 49%). 1H NMR (CDCl3, 400 MHz) δ 8.81 (s, 1H), 3.47 (m, 1H), 3.20 (m, 1H), 3.05 (m, 1H), 2.41 (m, 11H), 1.86 (m, 3H), 1.47 (m, 3H).

Aufarbeitung

  1. temperaturewas refluxed for 5 minutes
  2. customThe excess POCl3 was removed under vacuum
  3. dissolutionthe residue was dissolved in DCM (50 mL)
  4. additionThe mixture was then added to saturated NaHCO3 (200 mL)
  5. extractionThe aqueous phase was extracted with DCM (3×100 mL)
  6. customthe combined organic phases were dried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b57ccfeb121b45429c3a6adc65eca97f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846683B2

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