1,4-Dioxane hydrochloride → 5-(cyclopropylethynyl)-2-(piperazin-1-yl)pyrimidine HCl salt

HRID 522660Notes

Reaction equation

HRID 522660 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[N:8][C:9]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[N:10][CH:11]=2)[CH2:3][CH2:2]1.[ClH:25].O1CCOCC1>O1CCOCC1>[ClH:25].[CH:1]1([C:4]#[C:5][C:6]2[CH:7]=[N:8][C:9]([N:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)=[N:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118022323Tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 1180236485-(cyclopropylethynyl)-2-(piperazin-1-yl)pyrimidine HCl salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate (150 mg, 0.46 mmol) in dioxane (3 mL) was added 4 M HCl-dioxane (3 mL), and the reaction mixture was stirred room temperature for 1 hour. LCMS showed the reaction was completed. The reaction mixture was concentrated to afford 5-(cyclopropylethynyl)-2-(piperazin-1-yl)pyrimidine HCl salt as a white solid (100 mg, crude), which was directly used in the next step without further purification. MS (ES+) C13H16N4 requires: 228, found: 229 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d3c6d397f2a94875a14857a01c6f7f53
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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