Hydrochloric Acid → HCID 58016005, compound

HRID 2189338Notes

Reaction equation

HRID 2189338 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([N+:14]([O-])=O)=[CH:4][N:3]=1.[Sn](Cl)Cl.Cl>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([NH2:14])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 58015804HCID 58015804, compound

Product 1

HCID 58016005HCID 58016005, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2-chloro-5-nitro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (1 g, 4.1 mmol) in anhydrous EtOH (50 mL) is added Tin(II) chloride (2.3 g, 12.3 mmol) and concentrated HCl (1 mL) at ambient temperature. The reaction is heated to 80° C. for 1 h and quenched with 1N NaOH at 0° C. The mixture is extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo to give 0.5 g of (2-chloro-5-amino-pyrimidin-4-yl)-(1-ethyl-propyl)-amine. The crude is used as is.

Workup

  1. customquenched with 1N NaOH at 0° C
  2. extractionThe mixture is extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc779a3bcf674db990ae252581ab45cc
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…