Hydrochloric Acid → 4-(4-Amino-3-iodo-1h-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone

HRID 897451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897451
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:15]4=[N:16][CH:17]=[N:18][C:19]([NH2:20])=[C:14]4[C:13]([I:21])=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC(C)=O>[NH2:20][C:19]1[N:18]=[CH:17][N:16]=[C:15]2[N:11]([CH:8]3[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]3)[N:12]=[C:13]([I:21])[C:14]=12

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 223470211-(1,4-dioxaspiro[4.5]dec-8-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine2×

Produkt 1

HCID 223467294-(4-Amino-3-iodo-1h-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanoneAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (intermediate N) (13.12 g, 32.7 mmol) was suspended in acetone (240 mL) and the mixture was cooled to 0° C. Added aqueous 5 N HCl (200 mL) dropwise, keeping the temperature less than 4° C. during the addition. After the addition was complete the mixture was allowed to come to ambient temperature and stirred for 18 hours. The remaining solid was removed by filtration, and the filtrate was neutralized with saturated aqueous sodium bicarbonate. The precipitate was collected by filtration and washed with water and dried in vacuo to give 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanone (8.20 g, 32.8 mmol): 1H NMR (DMSO-d6, 400 MHz) 8.23 (s, 1H), 5.18 (m, 1H), 2.64-2.73 (m, 2H), 2.26-2.37(m, 4H), 2.17-2.30 (m, 2H).

Aufarbeitung

  1. customthe temperature less than 4° C.
  2. additionduring the addition
  3. additionAfter the addition
  4. customto come to ambient temperature
  5. customThe remaining solid was removed by filtration
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19a1156ada2e48e9a36bc977fdb211f6
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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