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

HRID 432141Notes

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

Conditions

Temperature: 0 °C

Procedure

1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Compound 9) (3.80 g, 8.57 mmol) was suspended in 190 ml of acetone and cooled to 0° C. 48 ml of 5.0N hydrochloric acid was added slowly through an additional funnel. The ice-water bath was removed and reaction mixture was stirred at room temperature overnight. Acetone was removed and aqueous layer was neutralized with 1.0N sodium hydroxide to PH about 10. The solid was filtered and dried to give 2.926 g of 4-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanone. 1H NMR (CDCl3) 2.39 (m, 2H), 2.62 (m, 6H), 5.3 0 (m, 1H), 6.08 (bs, 2H), 7.09 (m, 2H), 7.15 (m, 3H), 7.42 (m, 2H), 7.64 (d, J=8.70 Hz, 2H), 8.39 (s, 1H); LC/MS (MH+=400).

Workup

customThe ice-water bath was removed
customreaction mixture
customAcetone was removed
filtrationThe solid was filtered
customdried

Sources & evidence

ORD record: ord-091cce5fde494e4aa653e19798a87d3f
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660744B1

Reaction notes

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