Hydrochloric Acid → HCID 85994846, compound

HRID 530101Notes

Reaction equation

HRID 530101 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:9]([CH3:15])([C:11](OC)=[O:12])[CH3:10])[C:5]([N+:21]([O-])=O)=[CH:4][N:3]=1.Cl>C(O)C.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:21][C:11](=[O:12])[C:9]([CH3:15])([CH3:10])[N:8]([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89560709HCID 89560709, compound

Product 1

HCID 85994846HCID 85994846, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of methyl N-(2-chloro-5-nitropyrimidin-4-yl)-2-methyl-N-(3-methylbutyl)alaninate (2.0 g, 5.8 mmol) in ethanol (125 mL) was added iron powder (3.2 g, 58 mmol), the resulting mixture was heated to reflux. 1N aqueous hydrochloric acid was added to the reaction mixture (added in small portions, 5.0 ml total), The reaction mixture was heated at reflux until the completion of the reaction as monitored by TLC. The reaction was cooled to room temperature and filtered. The filtrate was evaporated to give a residue which was triturated using isopropyl ether to give titled compound (yield: 65%). 1HNMR (300 MHz, CDCl3): δ 0.97 (s, 3H), 1.0 (s, 3H), 1.37-1.56 (m, 7H), 1.65-1.80 (m, 2H), 3.52-3.58 (m, 2H), 7.62 (s, 1H), 9.13 (br s, 1H).

Workup

  1. temperaturethe resulting mixture was heated to reflux
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux until the completion of the reaction
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customto give a residue which
  7. customwas triturated

Sources & evidence

ORD record
ord-887f1bc397f247e2aab2ba027f2ffe27
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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