Hydrochloric Acid → HCID 89561473, compound

HRID 530125Notes

Reaction equation

HRID 530125 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:5]([N+:14]([O-])=O)=[CH:4][N:3]=1.Cl>C(O)C.[Fe]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH:11]([CH3:12])[CH3:13])[C:5]([NH2:14])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89561451HCID 89561451, compound

Product 1

HCID 89561473HCID 89561473, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2-chloro-N-(3-methylbutyl)-5-nitropyrimidin-4-amine (800 mg, 3.27 mmol) in ethanol (40 ml) was added iron powder (1.8 g). The resulting mixture was heated to reflux before 2 N aqueous hydrochloric acid (4 mL) was added in small portion over 10 min. The reaction was then refluxed for 2 h. The reaction mixture was cooled to rt, filtered to remove inorganic material. The solution was then concentrated under reduced pressure to afforded the desired compound (500 mg), which was used for next step without any further purifications. 1H NMR (CDCl3, 300 MHz) δ 0.92 (d, J=6.8 Hz, 6H), 1.42-1.80 (m, 3H), 3.42-3.60 (m, 2H), 5.01-5.15 (br s 1H), 7.60 (s, 1H).

Workup

  1. temperatureThe resulting mixture was heated
  2. additionwas added in small portion over 10 min
  3. temperatureThe reaction was then refluxed for 2 h
  4. filtrationfiltered
  5. customto remove inorganic material
  6. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-38f266c459624a25aa67ec9fb064d18a
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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