Methanol → HCID 58072938, compound

HRID 471412Notes

Reaction equation

HRID 471412 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:20].[Cs+].[Cs+].CO>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>[NH2:16][C:13]1[N:12]=[CH:11][C:10]([C:9]#[C:8][C:7]2[C:2]([C:14]3[CH:15]=[CH:10][C:11]([C:19]([OH:22])=[O:20])=[N:12][CH:13]=3)=[N:3][CH:4]=[N:5][C:6]=2[CH2:17][CH3:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 58073044HCID 58073044, compound

Product 1

HCID 58072938HCID 58072938, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

The title compound is synthesized in analogy to general procedure GP4 starting from 1.2 g (4.63 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine using 1.0 g (5.6 mmol) 4-methoxycarbonyl-3-pyridyl boronic acid, 163 mg (0.23 mmol) bis-(triphenylphoshine)palladium(II) chloride, 7.0 mL (13.9 mmol) of an aqueous 2 M Cs2CO3 and 2 mL MeOH in 10 mL DME. The reaction mixture is stirred over night at 80° C. The reaction mixture is poured on water and washed with DCM. Aqueous 1 M HCl is added to the aqueous phase until pH 5 is reached. The precipitated product is filtered off and washed with water and methanol. After drying 290 mg (13%) of the desired product are obtained a solid material which is used for the next step without further purification.

Workup

  1. additionThe reaction mixture is poured on water
  2. washwashed with DCM
  3. additionAqueous 1 M HCl is added to the aqueous phase until pH 5
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water and methanol
  6. dry with materialAfter drying 290 mg (13%) of the desired product
  7. customare obtained a solid material which
  8. customis used for the next step without further purification

Sources & evidence

ORD record
ord-f9c5b6357de24693ab5a0f2a1e43babf
Source dataset
uspto-grants-2014_01
Patent number
US08633183B2

Reaction notes

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