2-Bromoanisole → HCID 57869973, compound

HRID 1045690Notes

Reaction equation

HRID 1045690 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]([CH3:13])[C:11](=[O:14])[CH:10]=[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[N:8]=2)[CH2:3]1.Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29].CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]([CH3:13])[C:11](=[O:14])[CH:10]=[C:9]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)[N:8]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 113582-BromoanisoleHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57870047HCID 57870047, compound

Product 1

HCID 57869973HCID 57869973, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-((R)-3-aminopyrrolidin-1-yl)-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.20 g, 0.74 mmol), 2-bromoanisole (0.13 g, 0.74 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (0.061 g, 0.059 mmol), sodium tertbutoxide (0.10 g, 1.03 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.11 g, 0.18 mmol) in toluene (12 ml) and dioxane (2 ml) was stirred for 19 hours at 90° C. The solvent was evaporated off under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate/methanol=5/1) to afford 2-[(R)-3-(2-methoxyphenylamino)pyrrolidin-1-yl]-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.083 g, 29%) as colorless crystals.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate/methanol=5/1)

Sources & evidence

ORD record
ord-355a3dede4a643058f3b8b76a4952f96
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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