Cesium carbonate → HCID 59627218, compound

HRID 1523247Notes

Reaction equation

HRID 1523247 reaction equation
[CH2:1]([C@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH3:11])[C:6](=[O:19])[NH:5]1)[CH:2]=[CH2:3].[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([C:31]3[CH:30]=[CH:29][C:28]([F:27])=[CH:33][C:32]=3[F:34])=[CH:14][CH:13]=2)[CH3:11])[C:6](=[O:19])[NH:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343342,4-Difluorophenylboronic acidHCID 59627209HCID 59627209, compound

Product 1

HCID 59627218HCID 59627218, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (188 mg, 0.452 mmol), 2,4-difluorophenylboronic acid (86 mg, 0.581 mmol), Pd(Ph3P)2Cl2 (20 mg) and aqueous Cs2CO3 solution (0.5 mL, 2 M) in 1,4-dioxane (10 mL) was stirred and heated at reflux for 2 h. The organic phase was separated, and concentrated to give the crude product, which was purified by preparative TLC to give (R)-4-allyl-1-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (120 mg, 59%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. customThe organic phase was separated
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-1376a0b460494452a500e3fcc3d7418b
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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