Ethyl orthoformate → HCID 178480782, compound

HRID 1045768Notes

Reaction equation

HRID 1045768 reaction equation
[Br:1][C:2]1[C:3]([NH2:16])=[C:4]([NH2:15])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH:17](OCC)(OCC)OCC>>[Br:1][C:2]1[C:3]2[NH:16][CH:17]=[N:15][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 584469905-Bromo-2-(4-methyl-1-piperazinyl)-3,4-pyridinediamine

Product 1

HCID 178480782HCID 178480782, compoundYield 79%

Conditions

Temperature
130 °C

Procedure

A 100 mL round bottom flask was charged with 5-bromo-2-(4-methylpiperazin-1-yl)pyridine-3,4-diamine (1.1 g, 3.8 mmol) and triethyl orthoformate (20 mL). The resulting mixture was stirred at 130° C. for 1 h. Reaction progress was monitored by TLC (EtOAc/petroleum ether=2:1). Work-up: the reaction mixture was concentrated in vacuo. The residue was re-dissolved in EtOAc (50 mL) and washed with brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 10-40% EtOAc in CH2Cl2, to afford 0.9 g (79%) of the product as a white solid. MS m/z: 296 (M+H+).

Workup

  1. customReaction progress
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was re-dissolved in EtOAc (50 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with 10-40% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-a1764a9570b245dfbb264b97a248384a
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

Loading…