Sodium Carbonate → HCID 86694415, compound

HRID 535425Notes

Reaction equation

HRID 535425 reaction equation
[CH3:1][N:2]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:3]([CH3:28])[C:4]([NH:6][C:7]1[N:12]=[C:11]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[C:10](B(O)O)=[CH:9][CH:8]=1)=[O:5].Br[C:37]1[C:38]([CH3:44])=[N:39][CH:40]=[N:41][C:42]=1[CH3:43].C([O-])([O-])=O.[Na+].[Na+].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.O.CO>[C:32]([O:31][C:29](=[O:30])[N:2]([CH:3]([CH3:28])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:37]2[C:38]([CH3:44])=[N:39][CH:40]=[N:41][C:42]=2[CH3:43])=[C:11]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[N:12]=1)=[O:5])[CH3:1])([CH3:35])([CH3:34])[CH3:33]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 149222215-Bromo-4,6-dimethylpyrimidineHCID 86694416HCID 86694416, compound

Product 1

HCID 86694415HCID 86694415, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [6-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-(2-naphthalen-2-ylethynyl)pyridin-3-yl]boronic acid D2b (50 mg, 0.11 mmol), 5-bromo-4,6-dimethylpyrimidine (26 mg, 0.14 mmol), Dichlorobis(triphenylphosphine)-palladium(II) (8 mg, 0.01 mmol), Na2CO3 (34 mg, 0.32 mmol), dioxane (0.9 ml), MeOH (0.3 ml) and water (0.1 ml) is stirred under argon atmosphere for 2 h at 80° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 12 mg (21%). HPLC-MS: M+H=536; tR=2.22 min (*Method—6).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-f8703db07e6b43a684618dae75ab0fe4
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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