Water → 5-Benzyl-6-(1-bromo-propyl)-3-methyl-5h-isoxazolo[5,4-d]pyrimidin-4-one

HRID 1794593

Reaktionsgleichung

Reaktionsgleichung von HRID 1794593
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:17][C:11]=2[N:10]=[C:9]1[CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])=O.[Na+].[Br:27]Br.O>CC(O)=O>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:17][C:11]=2[N:10]=[C:9]1[CH:19]([Br:27])[CH2:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 222222815-Benzyl-3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one

Produkt 1

HCID 222223445-Benzyl-6-(1-bromo-propyl)-3-methyl-5h-isoxazolo[5,4-d]pyrimidin-4-oneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of the compound of Example 1, Step 3 (525 mg, 1.85 mmol) in HOAc (20 mL) at room temperature was treated with NaOAc (182 mg, 2.22 mmol) followed by Br2 (296 mg, 1.85 mmol). The mixture was stirred at 55° C. for 72 h then cooled and poured into water. The resulting precipitate was collected and air dried to afford the desired product as a white solid (200 mg, 30%); 1H NMR (DMSO-d6) δ 7.35 (m, 5H), 5.71 (d, J=16.5 Hz, 1H), 5.21 (d, J=16.5 Hz, 1H), 5.16 (t, J=7.5 Hz, 1H), 2.51 (s, 3H), 2.49 (m, 1H), 2.28 (m, 1H), 0.78 (t, J=7.5 Hz, 3H); LC/MS (ESI): 284 (M+H)+.

Aufarbeitung

  1. temperaturethen cooled
  2. customThe resulting precipitate was collected
  3. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-c399b84780fd458bb9ebc9f438372e4b
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022850B2

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