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tert-Butyl acetate → (6-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl)-5-methyl-pyridin-3-yl)-acetic acid tert-butyl ester

HRID 2195062
Notes
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Reaction equation

HRID 2195062 reaction equation
C1([N-]C2CCCCC2)CCCCC1.[Li+].[C:15]([O:19][C:20](=[O:22])[CH3:21])([CH3:18])([CH3:17])[CH3:16].Br[C:24]1[CH:25]=[C:26]([CH3:56])[C:27]([N:30]2[CH2:35][CH2:34][N:33]([C:36]3[CH:41]=[C:40]([C:42]4[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=4)[N:39]=[C:38]([N:49]4[CH2:53][CH2:52][CH2:51][C@H:50]4[CH3:54])[N:37]=3)[C@H:32]([CH3:55])[CH2:31]2)=[N:28][CH:29]=1.CC(P(C(C)(C)C)C(C)(C)C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:15]([O:19][C:20](=[O:22])[CH2:21][C:24]1[CH:29]=[N:28][C:27]([N:30]2[CH2:35][CH2:34][N:33]([C:36]3[CH:41]=[C:40]([C:42]4[CH:43]=[CH:44][C:45]([F:48])=[CH:46][CH:47]=4)[N:39]=[C:38]([N:49]4[CH2:53][CH2:52][CH2:51][C@H:50]4[CH3:54])[N:37]=3)[C@H:32]([CH3:55])[CH2:31]2)=[C:26]([CH3:56])[CH:25]=1)([CH3:18])([CH3:17])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10908tert-Butyl acetateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 10932176Lithium dicyclohexylamideHCID 591682874-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

Product 1

HCID 59168306
(6-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl)-5-methyl-pyridin-3-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To lithium dicyclohexyl amide add a solution of acetic acid tert-butyl ester (62 μL, 0.46 mmol) in toluene (2 mL). Stir for 10 min at room temperature, and then add 4-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine (200 mg, 0.38 mmol), Pd2(dba)3 (3.5 mg, 1%) and P(t-bu)3 (0.8 mg, 1%). De-gas the suspension for 5 min and stir for 16 h at room temperature. Dilute with EtOAc, wash with brine, dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify using flash chromatography eluting with EtOAc-Hexanes (1:4) to give the title ester.

Workup

  1. customDe-gas the suspension for 5 min
  2. stirringstir for 16 h at room temperature
  3. additionDilute with EtOAc
  4. washwash with brine
  5. dry with materialdry the organic layer (Na2SO4)
  6. concentrationconcentrate under reduced pressure
  7. customPurify
  8. washeluting with EtOAc-Hexanes (1:4)

Sources & evidence

ORD record
ord-729ce6f6bb3543c8994cbb1124e91e8c
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08334382B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes