Hydrochloric Acid → HCID 89570388, compound

HRID 530104Notes

Reaction equation

HRID 530104 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:11](OC)=[O:12])[CH3:10])[C:5]([N+:15]([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:15][C:11](=[O:12])[C@@H:9]([CH3:10])[NH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89561488HCID 89561488, compound

Product 1

HCID 89570388HCID 89570388, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of methyl N-(2-chloro-5-nitropyrimidin-4-yl)-D-alaninate (5 g, 19.2 mmol) in ethanol (400 mL) was added iron powder (7.14 g, 127 mmol). The resulted mixture was heated to reflux, followed by addition of 1M aqueous hydrochloric acid (15 ml) in small portions. The mixture was refluxed for 2 h. Then it was cooled to rt, the insoluble material was filtered off to give a clear solution. The solvent was evaporated to give a crude residue, which was then purified by silica gel flash chromatography (eluent: 5% methanol in dichloromethane) to give desired product (Yield: 81%). 1HNMR (300 MHz, DMSO d6): δ 1.34 (d, J=6.9 Hz, 3H), 4.22 (q, J=1.2 Hz, 1H), 7.50 (s, 1H), 8.45 (s, 1H) and 10.59 (s, 1H).

Workup

  1. temperatureThe resulted mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 2 h
  4. filtrationthe insoluble material was filtered off
  5. customto give a clear solution
  6. customThe solvent was evaporated
  7. customto give a crude residue, which
  8. customwas then purified by silica gel flash chromatography (eluent: 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6578f7628f7a42838840a45d84986b49
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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