6-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one → 6-(2,6-dichlorophenyl)-2-[(2,3-dihydro-6-benzofuranyl)amino]-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1176196Notes

Reaction equation

HRID 1176196 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[O:25]1[C:29]2[CH:30]=[C:31]([NH2:34])[CH:32]=[CH:33][C:28]=2[CH2:27][CH2:26]1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14]([NH:34][C:31]3[CH:32]=[CH:33][C:28]4[CH2:27][CH2:26][O:25][C:29]=4[CH:30]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 123690442,3-Dihydro-1-benzofuran-6-amine

Product 1

HCID 177473236-(2,6-dichlorophenyl)-2-[(2,3-dihydro-6-benzofuranyl)amino]-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 g of compound of formula (II), 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, and 352 mg of the compound of formula (III), (2,3-dihydro-6-benzofuranyl)amine, are heated at 80° C. in 10 ml of acetic acid for 1 h 30. After returning to ambient temperature, the medium is filtered in order to remove an impurity, diluted with water and ethyl acetate and brought to pH 9 with NaHCO3. The organic phase is then washed with a saturated NaCl solution, dried over Na2SO4 and concentrated under vacuum. The residue is chromatographed on silica (gradient: heptane 100 to heptane/ethyl acetate 40:60) to give 201 mg of the expected product in the form of a yellow solid.

Workup

  1. customAfter returning to ambient temperature
  2. filtrationthe medium is filtered in order
  3. customto remove an impurity
  4. additiondiluted with water and ethyl acetate
  5. washThe organic phase is then washed with a saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue is chromatographed on silica (gradient: heptane 100 to heptane/ethyl acetate 40:60)

Sources & evidence

ORD record
ord-8f340869c03c4a7a9f191a3b7f9b197b
Source dataset
uspto-grants-2010_11
Patent number
US07842806B2

Reaction notes

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