Sodium Carbonate → 4-Chloro-6-thiophen-2-yl-pyrimidine

HRID 910686Notes

Reaction equation

HRID 910686 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[Cl:1][C:2]1[CH:7]=[C:6]([C:10]2[S:9][CH:13]=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 709434,6-DichloropyrimidineHCID 27339602-Thiopheneboronic acid

Product 1

HCID 249021114-Chloro-6-thiophen-2-yl-pyrimidine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a flask fitted with a condenser was added 4,6-dichloro-pyrimidine (500 mg, 3.36 mmol), thiophene-2-boronic acid (429 mg, 3.36 mmol), Pd(OAc)2 (38 mg, 0.17 mmol), Ph3P (88 mg, 0.34 mmol), 1 M Na2CO3 (10.4 mL, 10.4 mmol), and DME (20 mL). The resulting mixture was heated at 100° C. for 18 h. After cooling, the resulting mixture was partitioned between CHCl3 (30 mL) and water (30 mL). The organic layer was dried and concentrated to yield a crude residue which was purified on SiO2 (0-30% EtOAc/hexanes) to yield 4-chloro-6-thiophen-2-yl-pyrimidine.

Workup

  1. customTo a flask fitted with a condenser
  2. temperatureAfter cooling
  3. customthe resulting mixture was partitioned between CHCl3 (30 mL) and water (30 mL)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto yield a crude residue which
  7. customwas purified on SiO2 (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e58be1cc4bc84ca287818d72a954836d
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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