tert-Butyl methyl ether → 6-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehyde

HRID 859623

Reaktionsgleichung

Reaktionsgleichung von HRID 859623
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH:7]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(OC)(C)(C)C>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH:11]=[O:12])[N:10]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 15413tert-Butyl methyl etherHCID 12217721Iodo benzene diacetateHCID 58762279(6-Methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Produkt 1

HCID 587626196-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehydeAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724126TempoKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A slurry of (6-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol (15.7 g, 95.6 mmol) from step 1 above, TEMPO (112 mg, 7.2 mmol), iodobenzene diacetate (33.9 g, 105.2 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 2 hours. Once the reaction was deemed complete, methyl tert-butyl ether (50 mL) was added slowly to precipitate the product. The concentrated mother liquor was introduced into a silica gel column and eluted with 2% MeOH/CH2Cl2 to give an additional amount of the aldehyde product as a white solid (12 g, 80%). 1H NMR (CDCl3) □: 2.54 (s, 3 H), 8.73 (s, 1 H), 8.85 (s, 1 H), 10.23 (s, 1 H).

Aufarbeitung

  1. customto precipitate the product
  2. additionThe concentrated mother liquor was introduced into a silica gel column
  3. washeluted with 2% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-4bcaf2c55b28420e9f7c3f4d2db82fb4
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151105B2

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