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

HRID 1916411Notes

Reaction equation

HRID 1916411 reaction equation
[ClH:1].O1CCOCC1.[OH:8][C@H:9]1[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].[CH3:31][C@H:11]1[C:12]2[C:17]([N:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)=[N:16][CH:15]=[N:14][C:13]=2[C@H:9]([OH:8])[CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59580343tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 66618034(5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl/dioxane (11.2 mL, 44.9 mmol) was added to a solution of tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (0.600 g, 1.79 mmol) in dioxane (15 mL). The reaction mixture was stirred at room temperature under nitrogen overnight (20 hours). The mixture was concentrated to dryness and dried on high vacuum line. The crude product was suspended in ether, sonicated, and stirred for 5 minutes. The solids were isolated by filtration through a medium frit funnel under nitrogen pressure, rinsed with ether, dried under nitrogen pressure, and dried further on a high vacuum line to give (5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride (0.440 g, 79.8% yield) as a powder. LC/MS (APCI+) m/z 235. The (5R,7S)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride was prepared using an analogous method.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customdried on high vacuum line
  3. customsonicated
  4. stirringstirred for 5 minutes
  5. customThe solids were isolated by filtration through a medium frit funnel under nitrogen pressure
  6. washrinsed with ether
  7. customdried under nitrogen pressure
  8. customdried further on a high vacuum line

Sources & evidence

ORD record
ord-2a1de92e3c1144cdbc41ca871bec1491
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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