1,4-Dioxane hydrochloride → HCID 178508631, compound

HRID 2105519Notes

Reaction equation

HRID 2105519 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.O1CCOCC1.[ClH:30]>>[Cl-:30].[Cl-:30].[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 (4A-2; 1.30 g, 4.08 mmol) in 4M HCl dioxane (12 mL) was stirred for 1 hr. The reaction was concentrated, triturated with ether to give 4-amino-1-piperidinium-4-yl-1H-pyrazolo[3,4-d]pyrimidin-2-ium dichloride. For free base: dissolved the above salt in H2O and passed through Dowex 1X2-400, ion-exchange resin (—OH form). The resin was washed with H2O then MeOH. The filtrate was concentrated and dried in vacuo to give pure 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-ef1f8d3d5a33426cab80d0784286a493
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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