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

HRID 897473Notes

Reaction equation

HRID 897473 reaction equation
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

Participants

4

Reactant 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

Product 1

HCID 223467624{-4-amino-3-[4-(2-pyrimidinyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-cyclohexanoneYield 88.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-786bf6d192b54d71a395f25cacb3c1d2
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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