Sodium Carbonate → HCID 178425190, compound

HRID 1501197Notes

Reaction equation

HRID 1501197 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][C@H:6]([C:8]1[CH:26]=[CH:25][C:11]([C:12]([NH:14][CH2:15][C:16]2[C:17]([OH:24])=[N:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])=[O:13])=[CH:10][CH:9]=1)[CH3:7].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][C:41]([NH2:44])=[N:42][CH:43]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:44][C:41]1[N:42]=[CH:43][C:38]([C:2]2[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=2)[O:5][C@H:6]([C:8]2[CH:26]=[CH:25][C:11]([C:12]([NH:14][CH2:15][C:16]3[C:17]([OH:24])=[N:18][C:19]([CH3:23])=[CH:20][C:21]=3[CH3:22])=[O:13])=[CH:10][CH:9]=2)[CH3:7])=[CH:39][N:40]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 178425186HCID 178425186, compound

Product 1

HCID 178425190HCID 178425190, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (S)-4-(1-(3-bromophenoxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (0.20 g, 0.44 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.13 g, 0.59 mmol), tetrakis(triphenylphosphine) palladium(0) (0.05 g, 0.04 mmol) in 1,4-dioxane (10 mL) and water (1.0 mL) was added sodium carbonate (0.14 g, 1.0 mmol). The reaction mixture was stirred at 90° C. for 12 hours. After the reaction, the reaction mixture was poured to the water (100 mL) and the product was extracted by dichloromethane (100 mL), concentrated and purified by column chromatography (silica gel:dichloromethane:methanol=12:1 with 1% ammonia aqueous solution) to give pure product (S)-4-(1-(3-(2-aminopyrimidin-5-yl)phenoxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (0.12 g, 60%) as a white solid. LR MS (M+H+): calcd for: 469.21. found 469.

Workup

  1. customAfter the reaction
  2. extractionthe product was extracted by dichloromethane (100 mL)
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica gel:dichloromethane:methanol=12:1 with 1% ammonia aqueous solution)

Sources & evidence

ORD record
ord-26e14fdf37f140899c278a19fe85083f
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…