Ammonium Chloride → HCID 67960627, compound

HRID 527674Notes

Reaction equation

HRID 527674 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[N:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=2)[O:5][CH2:4][CH2:3]1.[Cl-].[NH4+]>C1COCC1.O.[Fe]>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[N:14]=[CH:15][C:16]([NH2:19])=[CH:17][N:18]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67958114HCID 67958114, compound2×

Product 1

HCID 67960627HCID 67960627, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2-[(4-methyl-3,4-dihydro-2Hchromen-5-yl)oxy]-5-nitropyrimidine (Intermediate 216, 192 mg, 0.668 mmol) was dissolved in 9.0 mL of a 2/1 THF/water solution. Iron (187 mg, 3.34 mmol) and ammonium chloride (179 mg, 3.34 mmol) were added and the reaction mixture was stirred for 24 h at room temperature. After dilution with AcOEt and filtration over a celite pad (washing with AcOEt), the organic phase was washed (two times) with an aqueous saturated solution of NaHCO3. The organic layer was dried over Na2SO4, filtered and evaporated and the residue was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate from 1:0 to 0:1 as eluents affording the title compound (144 mg).

Workup

  1. filtrationAfter dilution with AcOEt and filtration
  2. washover a celite pad (washing with AcOEt)
  3. washthe organic phase was washed (two times) with an aqueous saturated solution of NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d2cef829b7c44969b8e0fef5394cf362
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…