tert-Butanol → tert-Butyl (5-methylpyrazin-2-yl)carbamate

HRID 1821737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821737
C[C:2]1[N:3]=[CH:4][C:5]([C:8](O)=O)=[N:6][CH:7]=1.C([N:13]([CH2:16]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[CH3:35][C:36]([OH:39])([CH3:38])[CH3:37]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:36]([O:39][C:16](=[O:25])[NH:13][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1)([CH3:38])([CH3:37])[CH3:35]

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Produkt 1

HCID 22046506tert-Butyl (5-methylpyrazin-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-methyl pyrazine carboxylic acid (13.8 g, 100 mmol) in 300 mL of toluene at room temperature under nitrogen was added triethyl amine (14 mL, 100 mmol) followed by diphenyl phosphoryl azide (21.6 mL, 100 mmol). After 30 min. at room temperature, 2-methyl-2-propanol (19 mL, 200 mmol) was added and the solution immersed in a 90° C. oil bath. After 2 hours, the reaction was cooled to RT, diluted to 600 mL with EtOAc, and washed 3×60 mL with 10% Na2CO3 and 1×600 mL with saturated NaCl. The organics were dried (MgSO4), filtered and concentrated to a yellow solid (17.5 g. 83%). 1H-NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 8.05 (s, 1H), 7.56(br s, 1H), 2.50 (s, 3H), 1.55 (s, 9H).

Aufarbeitung

  1. customimmersed in a 90° C.
  2. waitAfter 2 hours
  3. washwashed 3×60 mL with 10% Na2CO3 and 1×600 mL with saturated NaCl
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid (17.5 g. 83%)

Quellen und Nachweise

ORD-Eintrag
ord-6fd05748a38b4fe1b55f702617f381f2
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608618B2

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