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

HRID 1916416Notes

Reaction equation

HRID 1916416 reaction equation
[ClH:1].O1CCOCC1.[F:8][C:9]1([F:32])[C:13]2[N:14]=[CH:15][N:16]=[C:17]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[C:12]=2[C@H:11]([CH3:31])[CH2:10]1>O1CCOCC1>[ClH:1].[ClH:1].[F:32][C:9]1([F:8])[C:13]2[N:14]=[CH:15][N:16]=[C:17]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:12]=2[C@H:11]([CH3:31])[CH2:10]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

4M HCl/dioxane (2.27 mL, 9.09 mmol) was added 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 dioxane (2 mL.) The reaction mixture was stirred at room temperature overnight, after which it was concentrated to dryness and dried on under high vacuum 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 solid.

Workup

  1. concentrationafter which it was concentrated to dryness
  2. customdried on under high vacuum

Sources & evidence

ORD record
ord-552e5636f52e4c7a955ca139dada34fc
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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