Water → HCID 58394337, compound

HRID 2189199Notes

Reaction equation

HRID 2189199 reaction equation
Br[C:2]1[C:3]([NH:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:8][C:5]1[N:4]=[C:3]([NH:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[C:2]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58394392HCID 58394392, compound

Product 1

HCID 58394337HCID 58394337, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (S)-tert-butyl 3-(5-bromo-2-chloropyrimidin-4-ylamino)pyrrolidine-1-carboxylate (0.200 g, 0.539 mmol), phenylboronic acid (0.077 g, 0.636 mmol), PdCl2.dPPf (0.019 g, 0.026 mmol) and 1 M aqueous Na2CO3 (1.06 mL, 1.06 mmol) in DME (5.3 mL) was refluxed for 16 hours. After cooling, water (50 mL) was added and the aqueous phase was extracted with diethyl ether (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (40% ethyl acetate/hexanes) to give the title compound as an oil (0.163 g, 82%).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with diethyl ether (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-48674ecd660346ed972a42e2c62b7ae9
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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