Methanol → HCID 58072584, compound

HRID 632911Notes

Reaction equation

HRID 632911 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[C:6]([CH2:17][CH3:18])[N:5]=[CH:4][N:3]=1.[C:19]([O-:22])([O-])=O.[Cs+].[Cs+].[CH3:25][OH:26].CO[CH2:29][CH2:30][O:31][CH3:32]>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>[CH3:25][O:26][C:19](=[O:22])[C:29]1[CH:2]=[CH:7][C:6]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[C:6]([CH2:17][CH3:18])[N:5]=[CH:4][N:3]=2)=[CH:17][C:30]=1[O:31][CH3:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 58073044HCID 58073044, compound

Product 1

HCID 58072584HCID 58072584, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

The title compound is synthesized according to general procedure GP4 starting from 2.5 g (9.7 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine using 2.4 g (11.6 mmol) 3-methoxy-4-methoxycarbonylphenyl boronic acid, 339 mg (0.48 mmol) bis-(triphenylphoshine)palladium(II) chloride, 14 mL (28.2 mmol) of an aqueous 2 M Cs2CO3 and 5 mL MeOH in 50 mL DME. The reaction mixture is stirred for 2 hours at 90° C. The solvent is removed under reduced pressure and the residue is taken up in water and ethylacetate. The aqueous phase is extracted twice with ethylacetate. The combined organic layers are dried over MgSO4 filtered over celite and the solvent is removed under reduced pressure. After drying 3.3 g (89%) of the desired product is obtained.

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionThe aqueous phase is extracted twice with ethylacetate
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered over celite
  5. customthe solvent is removed under reduced pressure
  6. dry with materialAfter drying 3.3 g (89%) of the desired product
  7. customis obtained

Sources & evidence

ORD record
ord-ad239c9588594d1296e850b48d53cebb
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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