4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester → 4-(4-Fluoro-phenyl)-6-(2-(R)-methyl-piperazin-1-yl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

HRID 1444126Notes

Reaction equation

HRID 1444126 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:17]=[C:16]([N:27]3[CH2:31][CH2:30][CH2:29][C@H:28]3[CH3:32])[N:15]=2)[C@H:10]([CH3:33])[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[CH:19]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]3[CH3:33])[N:15]=[C:16]([N:27]3[CH2:31][CH2:30][CH2:29][C@H:28]3[CH3:32])[N:17]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 1

HCID 591682964-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 591683354-(4-Fluoro-phenyl)-6-(2-(R)-methyl-piperazin-1-yl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

Stir 4-[6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester (4.5 g, 9.88 mmol) in 4M HCl-dioxane (50 mL) for 40 min. Concentrate and partition between EtOAc and sat. NaHCO3. Dry the organic layer (Na2SO4) and concentrate under reduced pressure to yield the title compond.

Workup

  1. concentrationConcentrate
  2. custompartition between EtOAc and sat. NaHCO3
  3. dry with materialDry the organic layer (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customto yield the title compond

Sources & evidence

ORD record
ord-91eca25005564a38905dab0196594cb6
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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