Sodium Carbonate → HCID 67469534, compound

HRID 1522627Notes

Reaction equation

HRID 1522627 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[F:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1B(O)O>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>[F:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 43021752-Chloro-5-methylpyrimidin-4-amine

Product 1

HCID 67469534HCID 67469534, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
95 °C

Procedure

Bis(triphenylphosphine)palladium chloride (0.733 g, 1.045 mmol), 2-chloro-5-methylpyrimidin-4-amine (1.5 g, 10.45 mmol), Na2CO3 (5.22 mL, 10.45 mmol) and 2,5-difluorophenylboronic acid (2.145 g, 13.58 mmol) were combined and heated at 95° C. overnight. The reaction was filtered warm through a pad of Celite®, the solids rinsed with dioxane (3×25 mL) and the filtrate was concentrated directly onto a silica chromatography column which was then eluted with EtOAc (0-100%) in hexanes afforded 2-(2,5-difluorophenyl)-5-methylpyrimidin-4-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (d, J=0.76 Hz, 3H) 6.82 (br. s., 2H) 7.26-7.33 (m, 2H) 7.57-7.64 (m, 1H) 8.06 (d, J=0.76 Hz, 1H). MS [M+H] found 222.2.

Workup

  1. filtrationThe reaction was filtered
  2. temperaturewarm through a pad of Celite®
  3. washthe solids rinsed with dioxane (3×25 mL)
  4. concentrationthe filtrate was concentrated directly onto a silica chromatography column which
  5. washwas then eluted with EtOAc (0-100%) in hexanes

Sources & evidence

ORD record
ord-e2efb43af228442d9bb5e3197978c411
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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