1,4-Dioxane hydrochloride → (R)-7,7-difluoro-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine dihydrochloride

HRID 82393Notes

Reaction equation

HRID 82393 reaction equation
[F:1][C:2]1([F:25])[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:5]=2[C@H:4]([CH3:24])[CH2:3]1.[ClH:26].O1CCOCC1>O1CCOCC1>[ClH:26].[ClH:26].[F:25][C:2]1([F:1])[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:5]=2[C@H:4]([CH3:24])[CH2:3]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66845040HCID 66845040, compound

Product 1

HCID 66846210(R)-7,7-difluoro-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine dihydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-tert-butyl 4-(7,7-difluoro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (0.092 g, 0.260 mmol) in 2 mL dioxane was added 4M HCl/dioxane (2.27 ml, 9.09 mmol). The reaction mixture was stirred at room temperature 16 hours, after which it was concentrated to dryness and dried in vacuo to give (R)-7,7-difluoro-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine dihydrochloride (0.079 g, 93.0% yield) as a pale yellow powder. MS (APCI+) m/z 255 [M+H]+.

Workup

  1. concentrationafter which it was concentrated to dryness
  2. customdried in vacuo

Sources & evidence

ORD record
ord-20db23635a1d4cbcba60a8a077538c2a
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

Loading…