Ethylenediamine → 2-[(2-Aminoethyl)amino]-4-(2,4-difluorophenyl)-8-(2-fluorophenyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 30084Notes

Reaction equation

HRID 30084 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:11]=2[N:12]=[C:13](S(C)(=O)=O)[N:14]=1.[CH2:31]([NH2:34])[CH2:32][NH2:33]>C1COCC1>[NH2:33][CH2:32][CH2:31][NH:34][C:13]1[N:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[C:10]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 597893274-(2,4-difluorophenyl)-8-(2-fluorophenyl)-2-(methylsulfonyl)-pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 597893332-[(2-Aminoethyl)amino]-4-(2,4-difluorophenyl)-8-(2-fluorophenyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,4-difluorophenyl)-8-(2-fluorophenyl)-2-(methylsulfonyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (30 mg, 0.070 mmol) in dry THF (1 mL) was added ethylenediamine (23 uL, 0.35 mmol). The white precipitate initially formed redissolved on stirring. The mixture was stirred for about 15 min at about 20° C. LC/MS showed no starting material. The solvent was evaporated and the residue redissolved in DCM (1 mL) and water (1 mL). The layers were separated and the aqueous phase was basified with 2M sodium hydroxide (1 mL). The aqueous phase was extracted with DCM (2×1 mL) and the combined organic layers were evaporated to give 28 mg (100%) of the title compound. LC-MS m/z 412 (M+H)+, 2.19 min (ret time).

Workup

  1. customThe white precipitate initially formed
  2. dissolutionredissolved
  3. stirringThe mixture was stirred for about 15 min at about 20° C
  4. customThe solvent was evaporated
  5. dissolutionthe residue redissolved in DCM (1 mL)
  6. customThe layers were separated
  7. extractionThe aqueous phase was extracted with DCM (2×1 mL)
  8. customthe combined organic layers were evaporated

Sources & evidence

ORD record
ord-6c2039c0f25e4b62bb2d907471c4abfc
Source dataset
uspto-grants-2008_09
Patent number
US07423042B2

Reaction notes

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