Hydrazine hydrate (1:1) → 4-[1-(2-Aminoethyl)imidazol-5-yl]-2-(3-chloroanilino)pyrimidine

HRID 1064308Notes

Reaction equation

HRID 1064308 reaction equation
O.NN.[Cl:4][C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[NH:8][C:9]1[N:14]=[C:13]([C:15]2[N:19]([CH2:20][CH2:21][N:22]3C(=O)C4=CC=CC=C4C3=O)[CH:18]=[N:17][CH:16]=2)[CH:12]=[CH:11][N:10]=1>CCO>[NH2:22][CH2:21][CH2:20][N:19]1[C:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:7]3[CH:33]=[CH:34][CH:35]=[C:5]([Cl:4])[CH:6]=3)[N:14]=2)=[CH:16][N:17]=[CH:18]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 222735062-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine

Product 1

HCID 222734814-[1-(2-Aminoethyl)imidazol-5-yl]-2-(3-chloroanilino)pyrimidineYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (54 ml, 1.73 mmol) was added to a suspension of 2-(3-chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine (Example 10; 163 mg, 0.37 mmol) in EtOH (5 ml) and the mixture was heated at reflux for 2 hours. The mixture was allowed to cool, the volatiles removed by evaporation and the residue purified by column chromatography eluting with DCM and 7M methanolic ammonia solution (90:10) to give the title compound 69 mg, (59%) as a solid product. NMR: 1.41 (brs, 2H), 2.99 (t, 2H), 4.55 (t, 2H), 7.00-7.09 (m, 2H), 7.22-7.35 (m, 3H), 7.65-7.70 (m, 2H), 7.73-7.78 (m, 1H), 8.39 (d, 1H); m/z: 315.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customthe volatiles removed by evaporation
  5. customthe residue purified by column chromatography
  6. washeluting with DCM and 7M methanolic ammonia solution (90:10)

Sources & evidence

ORD record
ord-1cda125ff947448ea51e1eaa24b9eb2e
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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