Hydrochloric Acid → 4-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanone

HRID 432152Notes

Reaction equation

HRID 432152 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[CH:33]=[CH:32][CH:31]=[CH:30][CH: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[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:25][CH:26]=3)[C:14]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 223467671-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine2×

Product 1

HCID 223468934-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanoneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(4-phenoxyphenyl)-pyrazolo[3,4d]pyrimidin4-ylamine (Compound 9) (4.2 g, 95 mmol) in acetone (200 mL) was added HCl (5N, 50 mL) dropwise. Stir at room temperature for 24 hrs. Evaporate the acetone and basify with NaOH (5N, 60 mL). Extract with EtOAc (3×200 mL). Dry, filter and evaporate to leave a solid which was triturated with EtOAc: Et2O (1:20) and filtered to give 4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclohexanone as a cream solid (3.4 g, 90%), m.pt. 203-205° C.1H NMR (400 MHz, d6-DMSO) 8.28 (1H, s), 7.66 (2H, m), 7.44 (2H, m), 7.08-7.20 (5H, m), 6.1-7.3 (2H, bs), 5.26 (1H, m), 2.71 (2H, m), 2.41 (4H, m), 2.24 (2H, m) HPLC: Tr=15.43 mins, 95%.

Workup

  1. customEvaporate the acetone
  2. extractionExtract with EtOAc (3×200 mL)
  3. customDry
  4. filtrationfilter
  5. customevaporate
  6. customto leave a solid which
  7. customwas triturated with EtOAc: Et2O (1:20)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0b5d2a57290a4f6aac4d92ef87595640
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

Loading…