Sodium Carbonate → HCID 45788098, compound

HRID 1887691Notes

Reaction equation

HRID 1887691 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[N:10]1[CH:15]=[C:14](B(O)O)[CH:13]=[N:12][CH:11]=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>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>[CH3:8][C:6]1[N:7]=[C:2]([C:14]2[CH:15]=[N:10][CH:11]=[N:12][CH:13]=2)[CH:3]=[C:4]([NH2:9])[N:5]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2867546-Chloro-2-methylpyrimidin-4-amineHCID 2795193(Pyrimidin-5-yl)boronic acid

Product 1

HCID 45788098HCID 45788098, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To a microwave vial were added 6-chloro-2-methylpyrimidin-4-amine (700 mg, 4.88 mmol), pyrimidin-5-ylboronic acid (725 mg, 5.86 mmol), PdCl2(PPh3)2 (684 mg, 0.97 mmol), dioxane (10 mL) and Na2CO3 (2 M, 7 mL, 14 mmol) under Argon. The vial was microwave heated for 1 h at 160° C. Water was added, and extracted with 10% MeOH/CHCl3 (3*50 mL). The organic layers were combined and concentrated under reduced pressure and the crude was purified by silica gel chromatography to yield the title compound as a white solid; MS (m/z): [M+H]+188.2.

Workup

  1. extractionextracted with 10% MeOH/CHCl3 (3*50 mL)
  2. concentrationconcentrated under reduced pressure
  3. customthe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-955aac83570247e1b9e707ac257b9db4
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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