Water → HCID 136068487, compound

HRID 2189202Notes

Reaction equation

HRID 2189202 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:5]=[CH:4][N:3]=1.[OH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].O>[Pd].COCCOC>[OH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 58394344HCID 58394344, compound

Product 1

HCID 136068487HCID 136068487, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (S)-tert-butyl 3-(2-chloropyrimidin-4-ylamino)pyrrolidine-1-carboxylate (0.120 g, 0.400 mmol), 2-hydroxyphenyl boronic acid (0.166 g, 1.20 mmol), palladium catalyst (0.013 g, 0.020 mmol), and 1 M aqueous Na2CO3 (0.80 mL, 0.80 mmol) in DME (4 mL) was refluxed for 24 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 (66% ethyl acetate/hexanes) to give the title compound as an oil (0.070 g, 49%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureAfter cooling
  3. extractionthe aqueous phase was extracted with diethyl ether (3×50 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (66% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8a12a8f2da9a4c2eb713773fd823e88e
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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