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1,3-Benzodioxol-5-amine → 2-(Benzo[1,3]dioxol-5-ylamino)-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3195
Notes
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Reaction equation

HRID 3195 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.[CH2:25]1[O:34][C:33]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=2[O:26]1>C(OCC)(=O)C>[O:34]1[C:33]2[CH:32]=[CH:31][C:29]([NH:30][C:14]3[N:15]=[CH:16][C:11]4[CH:10]=[C:9]([C:3]5[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=5[Cl:8])[C:22](=[O:23])[N:21]([CH3:24])[C:12]=4[N:13]=3)=[CH:28][C:27]=2[O:26][CH2:25]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 843101,3-Benzodioxol-5-amineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 116046182-(Benzo[1,3]dioxol-5-ylamino)-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (3.70 mmol) of 3,4-methylenedioxyaniline was heated, with stirring, in a 200° C. oil bath. The resulting solution was heated for 5 minutes and cooled to room temperature. Ethyl acetate (2 mL) was added, and some traces of solids were filtered. The crystals that slowly developed in the filtrate were filtered and washed with 2 mL of ethyl acetate; wt 0.080 g. The solid was purified to remove dark colors by silica gel chromatography, eluting with chloroform and then 50% hexane/ethyl acetate to obtain pure crystalline product; wt 0.054 g; mp 240°-241° C.

Workup

  1. temperaturewas heated
  2. temperatureThe resulting solution was heated for 5 minutes
  3. temperaturecooled to room temperature
  4. filtrationsome traces of solids were filtered
  5. filtrationwere filtered
  6. washwashed with 2 mL of ethyl acetate
  7. customThe solid was purified
  8. customto remove dark colors by silica gel chromatography
  9. washeluting with chloroform
  10. custom50% hexane/ethyl acetate to obtain pure crystalline product

Sources & evidence

ORD record
ord-229e6ead42474df5b581ec87f76dc9f1
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733914

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes