1,4-Dioxane hydrochloride → HCID 178508631, compound

HRID 604993Notes

Reaction equation

HRID 604993 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[N:9]=[CH:10][C:3]=12.[ClH:24].O1CCOCC1>>[Cl-:24].[Cl-:24].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:16][CH2:15][NH2+:14][CH2:13][CH2:12]3)[NH+:9]=[CH:10][C:3]=12

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67055613HCID 67055613, compound

Product 1

HCID 178508631HCID 178508631, compound

Procedure

A mixture of tert-butyl 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (1.30 g, 4.08 mmol) in 4M HCl/dioxane (12 mL) was stirred for one hour. The reaction was concentrated, triturated with ether to give 4-amino-1-piperidinium-4-yl-1H-pyrazolo[3,4-d]pyrimidin-2-ium dichloride. The free base was obtained by dissolution in water and passing this solution through a Dowex 1X2-400 ion-exchange resin (—OH form). The resin was washed with water and then methanol. The filtrate was concentrated and dried in vacuo to give pure 1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amine as the free base. 1H-NMR (500 MHz, d6 DMSO) δ 8.14 (s, 1H), 8.07 (s, 1H), 7.64 (bs, 2H), 4.57-4.67 (m, 1H), 3.05 (d, J=12.46 2H), 2.55-2.67 (m, 2H), 2.06 (bs, 1H), 1.90-2.12 (m, 2H), 1.73-1.80 (m, 2H). LRMS m/z (M+H) Calcd: 219.1, found: 219.1.

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated with ether

Sources & evidence

ORD record
ord-46eb5c1471af4d6186a558b9c82fe21a
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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