Ethanol → HCID 58073028, compound

HRID 632905Notes

Reaction equation

HRID 632905 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]([CH3:17])[N:5]=[CH:4][N:3]=1.[C:18]([O-:21])([O-])=O.[Cs+].[Cs+].[CH3:24][CH2:25]O.[CH3:27][OH:28]>COCCOC.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>[CH3:27][O:28][C:18](=[O:21])[C:25]1[CH:24]=[CH:2][C:7]([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]([CH3:17])[N:5]=[CH:4][N:3]=2)=[CH:6][CH:17]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 10796Cesium carbonateHCID 58072945HCID 58072945, compound

Product 1

HCID 58073028HCID 58073028, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

The title compound is synthesized according to general procedure GP4 starting from 2.0 g (8.2 mmol) 4-chloro-6-methyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine using 2.2 g (12.3 mmol) 4-methoxycarbonylphenyl boronic acid, 240 mg (1.5 mmol) 287 mg (0.41 mmol) bis-(triphenylphoshine)palladium(II) chloride, 6.1 mL (12.3 mmol) of an aqueous 2 M Cs2CO3 and 2 mL EtOH in 5 mL DME. The reaction mixture is stirred for 1 h at 130° C. in the microwave. The reaction mixture is suspended in MeOH and the precipitated to product is filtered off and washed with MeOH. After drying 2.2 g (77%) of the desired product are obtained as solid material.

Workup

  1. customthe precipitated to product
  2. filtrationis filtered off
  3. washwashed with MeOH
  4. dry with materialAfter drying 2.2 g (77%) of the desired product
  5. customare obtained as solid material

Sources & evidence

ORD record
ord-cefb552225524b2a996e5a4f0c2635c9
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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