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Methanol → HCID 66737912, Verbindung

HRID 1640660
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1640660
[CH:1]1([C:5]2[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]3=[C:7](I)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:16][OH:17].[CH:18](N(CC)C(C)C)(C)C.[OH2:27]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:14][C:13]1[C:8]2[N:9]([C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)=[N:6][C:7]=2[C:16]([O:27][CH3:18])=[O:17])[CH:10]=[CH:11][N:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 81531DiisopropylethylamineHCID 426093653-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine

Produkt 1

HCID 66737912HCID 66737912, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine (500 mg, 2 mmol) and tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.1 mmol) was degassed dry three times then treated with methanol (20 mL) and N,N-diisopropylethylamine (0.7 mL, 4.0 mmol) and the mixture heated at 70° C. under an atmosphere of carbon monoxide, with intermittent bubbling of this gas under the surface of the reaction mixture. After 3d heating with extensive bubbling through of the solution with carbon monoxide and some addition of fresh catalyst after day 2, TLC (10% MeOH/DCM) indicated the reaction to be complete. The reaction mixture was diluted with water, extracted with DCM and the extracts washed with water and brine, then dried over magnesium sulphate, and concentrated in vacuo to afford an orange solid which was recrystallised from acetonitrile to afford methyl 8-amino-3-cyclobutylimidazo[1,5-a]pyrazine-1-carboxylate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.97-2.06 (m, 1 H), 2.10-2.26 (m, 1 H), 2.43-2.54 (m, 2 H), 2.53-2.68 (m, 2 H), 3.78 (dd, J=9.09, 8.08 Hz, 1 H), 4.01 (s, 3H), 7.08 (d, J=4.80 Hz, 1 H), 7.22 (d, J=4.80 Hz, 1 H), 7.38 (br. s., 1 H), 7.69 (br. s., 1 H).

Aufarbeitung

  1. customdry three times
  2. customwith intermittent bubbling of this gas under the surface of the reaction mixture
  3. temperatureAfter 3d heating
  4. customwith extensive bubbling through of the solution with carbon monoxide
  5. additionsome addition of fresh catalyst after day 2, TLC (10% MeOH/DCM)
  6. customthe reaction
  7. extractionextracted with DCM
  8. washthe extracts washed with water and brine
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated in vacuo
  11. customto afford an orange solid which
  12. customwas recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a0aeff43a88d45bfa0e92937f98ef76d
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114846B2

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