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

HRID 469366Notes

Reaction equation

HRID 469366 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-chloropyrimidine-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

Sources & evidence

ORD record
ord-04090373bc6546358ffa2a2306c3b493
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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