Acetic Acid → HCID 178518861, compound

HRID 1271083Notes

Reaction equation

HRID 1271083 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][NH2:22])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:23](OC)(=[O:26])[CH:24]=[CH2:25].[K].C(O)(=O)C>C(O)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([N:21]4[CH2:25][CH2:24][C:23]([OH:26])=[N:22]4)[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7294Methyl AcrylateHCID 5462222PotassiumHCID 21948216HCID 21948216, compound

Product 1

HCID 178518861HCID 178518861, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

To a mixture of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (7.82 g, 0.025 mol) and Methyl acrylate (2.58 g, 0.030 mol) in tert BuOH (80 ml) is added Potassium tert-butoxyde (5.6 g, 0.05 mol) in portions at 25° C. After stirring for two hours the resulting brown solution is poured in water (500 ml), acidified with acetic acid and partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue is purified by crystallizing from acetone. The resulting precipitate is filtered with suction to yield the title compound. (1.55 g, 16.9%) m.p. 222–226° C.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is purified
  7. customby crystallizing from acetone
  8. filtrationThe resulting precipitate is filtered with suction

Sources & evidence

ORD record
ord-0fe304e106b84c819d0ba6c99c7890ff
Source dataset
uspto-grants-2007_04
Patent number
US07205301B2

Reaction notes

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