Water → (6-Chloro-pyrimidin-4-yl)-(7-methyl-2,3-dihydro-benzofuran-5-yl)-methanone

HRID 2096365Notes

Reaction equation

HRID 2096365 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:15][C:16]1[C:24]2[O:23][CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:18]2[CH:17]=[C:16]([CH3:15])[C:24]3[O:23][CH2:22][CH2:21][C:20]=3[CH:19]=2)=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 225923867-Methyl-2,3-dihydrobenzofuran

Product 1

HCID 58181093(6-Chloro-pyrimidin-4-yl)-(7-methyl-2,3-dihydro-benzofuran-5-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

0.396 g (2.24 mmol) 6-chloropyrimidin-4-carboxylic acid chloride and 0.328 g (2.46 mmol) aluminium trichloride in 10 mL DCM were stirred for 20 min at RT. Then 0.300 g (2.24 mmol) 7-methyl-2,3-dihydro-benzofuran in DCM were added dropwise to the reaction mixture and this was stirred for 1.5 h at RT. After the addition of water and DCM to the reaction mixture the phases were separated and the aqueous phase was extracted with DCM. The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution, dried on sodium sulphate, filtered and evaporated down i.vac.

Workup

  1. customwere separated
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated down i.vac

Sources & evidence

ORD record
ord-786c5ffffc684b228a777d55fc09e09e
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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