Phosphorus oxychloride → 5-Benzyl-4-chloro-6-methylpyrimidin-2-amine

HRID 965681

Reaktionsgleichung

Reaktionsgleichung von HRID 965681
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[N:3]=1.P(Cl)(Cl)([Cl:19])=O>>[CH2:9]([C:5]1[C:6]([Cl:19])=[N:7][C:2]([NH2:1])=[N:3][C:4]=1[CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178433370HCID 178433370, Verbindung

Produkt 1

HCID 8202385-Benzyl-4-chloro-6-methylpyrimidin-2-amineAusbeute 53,7 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-amino-5-benzyl-6-methylpyrimidine-4-ol (1.2 g, 5.57 mmol) and phosphorous oxychloride (9 ml) was kept to warm at 90° C. for 6 hours. The reaction mixture was concentrated in vacuo. Ice-water was added to the residue and an aqueous ammonia was cautiously added thereto. The solution was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=8:2) to give the object compound (700 mg, 53.7%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionIce-water was added to the residue
  3. additionan aqueous ammonia was cautiously added
  4. extractionThe solution was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=8:2)

Quellen und Nachweise

ORD-Eintrag
ord-c7619397166e40999cbc96988d58f78b
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951866B2

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