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

HRID 1049967Notes

Reaction equation

HRID 1049967 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-d961143e25f5495ab999d37a00e2f6df
Source dataset
uspto-grants-2016_07
Patent number
US09382277B2

Reaction notes

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