Citric Acid → 3-Amino-6-iodo-pyrazine-2-carboxylic acid dimethylamide

HRID 1693740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693740
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([I:8])=[CH:6][N:7]=1.[CH:12]([N:15](C(C)C)[CH2:16]C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CNC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C.C1COCC1.ClCCl>[CH3:12][N:15]([CH3:16])[C:9]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([I:8])[N:4]=1)=[O:11]

Komponenten

9

Edukt 5

HCID 311Citric AcidHCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 468356023-Amino-6-iodopyrazine-2-carboxylic acid

Produkt 1

HCID 575376613-Amino-6-iodo-pyrazine-2-carboxylic acid dimethylamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

534 mg (2.02 mmol) of 3-amino-6-iodo-pyrazine-2-carboxylic acid were dissolved in 20 mL of 50% v/v acetonitrile in dichloromethane containing 350 μL (2.01 mmol) of di-iso-propyl-ethylamine. 818 mg (2.18 mmol) of N,N,N′,N′,-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate were added. Upon stirring for 3 minutes at ambient temperature 2.5 mL (5 mmol) of 2.0 M dimethylamine in anhydrous THF was added and stirring was continued for 23 h. The resulting solution was distributed between dichloromethane and 10% w/v aqueous citric acid solution. The organic phase was dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes to afford 363 mg (1.24 mmol, 62%) of 3-amino-6-iodo-pyrazine-2-carboxylic acid dimethylamide as a pale yellow crystalline solid. 1H-NMR [500 MHz, d6-DMSO] δ: 8.25 (s, 1H), 6.71 (s, hr., 2H), 2.98 (s, 3H), 2.92 (s, 3H); MS [MH+] m/z: 293.

Aufarbeitung

  1. additionwas added
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3a65ccfff94e4934ad1b35ca1e8aafe4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158647B2

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