Ammonium Chloride → HCID 67960029, compound

HRID 527680Notes

Reaction equation

HRID 527680 reaction equation
[C:1]12([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[O:13][C:14]3[N:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=3)[O:6][CH2:5][CH2:4]1)[CH2:3][CH2:2]2.[Cl-].[NH4+]>C1COCC1.O.[Fe]>[C:1]12([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[O:13][C:14]3[N:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=3)[O:6][CH2:5][CH2:4]1)[CH2:2][CH2:3]2

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86698465HCID 86698465, compound2×

Product 1

HCID 67960029HCID 67960029, compoundYield 63.5%

Reagents, catalysts & solvents 2

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

Procedure

2-(2,3-dihydrospiro[chromene-4,1′-cyclopropan]-5-yloxy)-5-nitropyrimidine (Intermediate 222, 91 mg, 0.304 mmol) was dissolved in 9.0 mL of a 2/1 THF/water solution. Then iron (85 mg, 1.52 mmol) and ammonium chloride (81 mg, 1.52 mmol) were added and the reaction mixture was stirred at room temperature for 10 h. 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. The residue was purified by flash chromatography (Biotage system) on silica gel using cyclohexane to cyclohexane/ethyl acetate 1:1 as eluents affording the title compound (52 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 (Biotage system) on silica gel

Sources & evidence

ORD record
ord-89ba15dcff1a4b11a59b21d247520584
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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