Hydrochloric Acid → 4{-4-amino-3-[4-(2-pyrimidinyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-cyclohexanone

HRID 432183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432183
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]([C:21]4[CH:26]=[CH:25][C:24]([O:27][C:28]5[N:33]=[CH:32][CH:31]=[CH:30][N:29]=5)=[CH:23][CH:22]=4)=[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]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:25][CH:26]=3)[C:14]=12

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 223470101-(1,4-dioxaspiro[4.5]dec-8-yl)-3-[4-(2-pyrimidinyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 223467624{-4-amino-3-[4-(2-pyrimidinyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-cyclohexanoneAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A slurry of 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-[4-(2-pyrimidinyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (int BB) (1.22 g, 0.00274 mol) in acetone was cooled to 0° C. and 5 N aqueous hydrochloric acid (15 mL) was added dropwise keeping the temperature less than 5° C. After the addition was complete, the mixture was stirred at ambient temperature for three hours. The solution was filtered through celite and neutralized with a saturated aqueous solution of sodium bicarbonate. The precipitate which formed was filtered, washing with water and dried in vacuo overnight to give 4{-4-amino-3-[4-(2-pyrimidinyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-cyclohexanone as a white solid (0.937 g, 0.00243 mol): 1H NMR (DMSO-d6, 400 MHz) 8.68 (d, 2H), 8.29 (s, 1H), 7.56 (d, 2H), 7.37 (d, 2H), 7.31 (t, 1H), 6.30-7.20 (bs, 2H), 5.25-5.30 (m, 1H), 2.67-2.75 (m, 2H), 2.24-2.43 (m, 6H).

Aufarbeitung

  1. customthe temperature less than 5° C
  2. additionAfter the addition
  3. filtrationThe solution was filtered through celite
  4. customThe precipitate which formed
  5. filtrationwas filtered
  6. washwashing with water
  7. customdried in vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-e64265310a0142c9afec5a926a8453c6
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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