Sodium Carbonate → HCID 11587369, compound

HRID 628827Notes

Reaction equation

HRID 628827 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.[C:19]([O-:22])([O-])=[O:20].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]1([CH3:9])[CH:11]=[CH:12][CH:13]=[C:14]([C:6]2[N:7]=[CH:2][N:3]=[C:4]([C:10]3[CH:11]=[CH:12][C:13]([C:19]([OH:22])=[O:20])=[CH:14][CH:15]=3)[CH:5]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 27339503-Tolylboronic acid

Product 1

HCID 11587369HCID 11587369, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

Part A. A 50 mL three-neck round-bottom flask is charged with 2,4-dichloropyrimidine (0.58 g, 3.89 mmol), 3-methylphenylboronic acid (0.31 g, 2.28 mmol), Na2CO3 (0.73 g, 6.88 mmol), tetrakis(triphenylphosphine) palladium (13.0 mg, 1.12×10−2 mmol). The flask is evacuated, and refilled with N2. DMF (15 mL, anhydrous) is then added to the flask. The flask is evacuated again, and refilled with N2, repeated two times. The reaction is heated to 100° C. overnight. The reaction mixture is partitioned between ethyl ether and water. The organic layer is washed with brine, dried over MgSO4, and then removed. The residue is further purified by flash column chromatography, eluting with methylene chloride/hexanes (1:10) to afford 45.7 mg (5.8% yield) of desired product. The obtained compound (4-chloro-6-m-tolyl-pyrimidine) is >80% pure as determined by LC-MS. MS (ES+): m/e 205.23.

Workup

  1. customThe flask is evacuated
  2. additionrefilled with N2
  3. additionDMF (15 mL, anhydrous) is then added to the flask
  4. customThe flask is evacuated again
  5. additionrefilled with N2
  6. customThe reaction mixture is partitioned between ethyl ether and water
  7. washThe organic layer is washed with brine
  8. dry with materialdried over MgSO4
  9. customremoved
  10. customThe residue is further purified by flash column chromatography
  11. washeluting with methylene chloride/hexanes (1:10)

Sources & evidence

ORD record
ord-61f18a933cc245a3a98513717d21f997
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

Loading…