Methanol → HCID 58072584, compound

HRID 471423Notes

Reaction equation

HRID 471423 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-6c57ab7901024fc5ae1de918622461f5
Source dataset
uspto-grants-2014_01
Patent number
US08633183B2

Reaction notes

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