Hydrazine hydrate (1:1) → HCID 71268944, compound

HRID 1025380Notes

Reaction equation

HRID 1025380 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[C:27]([C:28]([O:30]CC)=O)=[C:26]([CH:33]=O)[N:25]=[C:24]([C:35]4[CH:40]=[CH:39][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:36]=4)[N:23]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:46][NH2:47]>C(O)C>[CH3:44][O:43][C:41]([C:38]1[CH:39]=[CH:40][C:35]([C:24]2[N:23]=[C:22]([NH:21][C:18]3[CH:17]=[CH:16][C:15]([CH2:14][N:11]4[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]4)=[CH:20][CH:19]=3)[C:27]3[C:28](=[O:30])[NH:47][N:46]=[CH:33][C:26]=3[N:25]=2)=[CH:36][CH:37]=1)=[O:42]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86677022HCID 86677022, compound

Product 1

HCID 71268944HCID 71268944, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(4-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)phenylamino)-6-formyl-2-(4-(methoxycarbonyl)phenyl)pyrimidine-5-carboxylate (0.5 g, 0.82 mmol) was dissolved in ethanol (5 mL), hydrazine hydrate (60 μL, 1.24 mmol) was added and the mixture is refluxed for 2.5 hours. The reaction mixture was cooled to obtain a solid precipitate. The precipitate was filtered and the solid dried under vacuum (0.4 g). 1H NMR (400 MHz, DMSO-d6): δ 13.41 (s, 1H), 11.52 (s, 1H), 8.52 (d, J=8.4 Hz, 2H), 8.34 (s, 1H), 8.13 (d, J=8.8 Hz, 2H), 7.86 (d, J=8.8 Hz, 2H), 7.42 (d, J=8.4 Hz, 2H), 3.90 (s, 3H), 3.51 (s, 2H), 3.29 (t, J=4.4 Hz, 4H), 2.34 (t, J=4.4 Hz, 4H), 1.39 (s, 9H); MS m/z 572.3 (M+1).

Workup

  1. temperaturethe mixture is refluxed for 2.5 hours
  2. temperatureThe reaction mixture was cooled
  3. customto obtain a solid precipitate
  4. filtrationThe precipitate was filtered
  5. customthe solid dried under vacuum (0.4 g)

Sources & evidence

ORD record
ord-996a37d55b1e4434aa6fd8af76ceec3d
Source dataset
uspto-grants-2014_05
Patent number
US08729079B2

Reaction notes

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