1,2-Dimethoxyethane → 2-Chloro-4-(2-chloropyridin-3-yl)pyrimidine

HRID 446292Notes

Reaction equation

HRID 446292 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[CH:12][N:11]=1.COCCOC.C([O-])(O)=O.[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:15]2[C:10]([Cl:9])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 775312,4-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 2762704(2-Chloropyridin-3-yl)boronic acid

Product 1

HCID 249019302-Chloro-4-(2-chloropyridin-3-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To 2,4-dichloropyrimidine (2.00 g, 13.4 mmol), 2-chloropyridine-3-boronic acid (3.16 g, 20.1 mmol) and Pd(PPh3)4 (1.55 g, 1.30 mmol), was added DME (30.0 mL) and 1 M NaHCO3 (13.0 mL). The resulting mixture was heated to 90° C. for 17 hours, then diluted with EtOAc and extracted with saturated sodium carbonate, water, and brine. The organics were dried over sodium sulfate, filtered and concentrated. The resulting solid was triturated with ether and dried to yield the title compound. MS m/z=226 [M+H]+. Calc'd for C9H5Cl2N4: 225.12.

Workup

  1. extractionextracted with saturated sodium carbonate, water, and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with ether
  6. customdried

Sources & evidence

ORD record
ord-b07a5ab80f9146d98261189d327ea825
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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