Ethylenediamine → 2-[(2-Aminoethyl)amino]-8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 30082

Reaction equation

HRID 30082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].[CH2:32]([NH2:35])[CH2:33][NH2:34]>C1COCC1.C(OCC)(=O)C.O>[NH2:34][CH2:33][CH2:32][NH:35][C:16]1[N:17]=[C:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[CH3:26])[C:13]2[CH:12]=[CH:11][C:10](=[O:31])[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[C:14]=2[N:15]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 596395772-[(2-Aminoethyl)amino]-8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 89.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

The title compound of Example 7 [8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one] (0.89 g, 0.002 mol) in dry THF, stirring at 23°, under Ar, was treated with ethylenediamine (668 uL, 0.01 mol). The color became bright orange. LC MS showed no starting material after 5 min. Reaction was stripped to dryness; the residue taken up in ethyl acetate-water. The layers were separated and the aqueous phase adjusted to pH 10.5 with 10% NaOH. Aqueous phase was extracted twice with ethyl acetate; combined organic layers were dried (Na2SO4), then evaporated to give 0.762 g (89%) of the title compound as an amber glass. LC MS (m/e)=426 (MH+). Rt=1.52 min.

Workup

  1. customafter 5 min
  2. customReaction
  3. customThe layers were separated
  4. extractionAqueous phase was extracted twice with ethyl acetate
  5. dry with materialcombined organic layers were dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-d53afcde56f746e2bc7c9b71ad878cb3
Source dataset
uspto-grants-2008_09
Patent number
US07423042B2

Linked notes

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