Stannous Chloride → HCID 59627820, compound

HRID 1907840Notes

Reaction equation

HRID 1907840 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[C:5]([N+:20]([O-])=O)=[CH:4][N:3]=1.Cl[Sn]Cl>C(O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[C:5]([NH2:20])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 59627819HCID 59627819, compound

Product 1

HCID 59627820HCID 59627820, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A suspension of 2-chloro-5-nitro-N-(quinolin-6-ylmethyl)pyrimidin-4-amine (2.25 g, 7.14 mmol), SnCl2 (7.18 g, 32 mmol) in ethanol (50 mL) and CHCl3 (10 mL) was refluxed for 5 h. The mixture was allowed to cool to room temperature and the solvent was evaporated. The residue was basified to pH 10 by saturated aqueous NaHCO3. The resulting suspension was stirred in ethanol (500 mL) for 2 h and filtered through a pad of silica gel. The filtrate was evaporated. Flash chromatography of the residue over silica gel, using 100% EtOAc to 10% MeOH-EtOAc with 0.5% NH3H2O, gave the desired product (1.02 g, 50%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 4.88 (s, 2H), 7.46-7.53 (m, 2H), 7.77-8.02 (m, 3H), 8.32 (d, 1H, J=8.0 Hz), 8.8 (m, 1H); LCMS (APCI) m/z 286.2 (M+H+).

Workup

  1. temperaturewas refluxed for 5 h
  2. customthe solvent was evaporated
  3. filtrationfiltered through a pad of silica gel
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2568a90112ab42899c3ca07d4b89f33e
Source dataset
uspto-grants-2013_12
Patent number
US08598184B2

Reaction notes

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