m-Chloroperbenzoic acid → 4'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidine

HRID 2359733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359733
[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:27])[N:12]=3)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 679837614'-(Cyclopropylmethyl)-2-(methylsulfanyl)-4,5'-bipyrimidine

Produkt 1

HCID 679831774'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4′-(cyclopropylmethyl)-2-(methylsulfanyl)-4,5′-bipyrimidine (4a) (62.5 mg, 0.242 mmol) in DCM (968 μl), mCPBA (65.1 mg, 0.290 mmol) was added and the reaction mixture was stirred at rt for 1 hour. The crude reaction mixture was partitioned between saturated sodium bicarbonate solution and DCM. The aqueous layer was separated and back-extracted twice with DCM. The combined organic extracts were washed with brine, dried over sodium sulfate, then concentrated in vacuo. The crude product was carried on to the next step without further purification. MS (ES+): m/z=275.2 (100) [MH+]. HPLC: tR=0.72 minute over 3 minutes. Purity: 100% [HPLC (LC/MS) at 220 nm].

Aufarbeitung

  1. customThe crude reaction mixture
  2. customwas partitioned between saturated sodium bicarbonate solution and DCM
  3. customThe aqueous layer was separated
  4. extractionback-extracted twice with DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was carried on to the next step without further purification
  9. waitHPLC: tR=0.72 minute over 3 minutes

Quellen und Nachweise

ORD-Eintrag
ord-1ceb9c9877844a778ec3275af32cf489
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685993B2

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