Acetone → HCID 86724359, compound

HRID 1482706Notes

Reaction equation

HRID 1482706 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=[O:23])[CH:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([F:25])=[CH:4][N:3]=1.CC(C)=O.[NH4+].[Cl-].CCCCCC.C(OCC)(=O)C>O.[Zn]>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][OH:23])[CH:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([F:25])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 21226206Ethyl acetate hexaneHCID 86724358HCID 86724358, compound

Product 1

HCID 86724359HCID 86724359, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-nitrophenyl)carbamate (0.78 g) in mixture of acetone (3 ml) and water (2 ml) was added NH4Cl (0.22 g) and the reaction mixture was heated to 60° C. Zn dust (289 mg) was added to the reaction mixture at 60° C. portion wise. The reaction mixture was stirred for 45 minute at 60° C. and monitored on TLC using hexane:ethyl acetate (3:7) as mobile phase. After completion of the reaction, the reaction mixture was poured in water. The product was extracted into ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate and concentrated completely under reduce pressure to give crude product. Crude material was purified by using column chromatography. Desired product eluted with 5% ethyl acetate in hexane to give, after concentration, 0.409 g of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(hydroxyamino)phenyl)carbamate. M+1=354.8. 1H NMR: DMSO-d6 (400 MHz): 1.400 (s, 9H), 6.612 (d, 1H, J=7.6), 6.688 (s, 1H), 6.774 (d, 1H, J=8.4), 7.170-7.210 (t, 1H, J=8), 8.434 (d, 2H, J=6.4), 8.95 (s, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionThe product was extracted into ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated completely
  6. customto give crude product
  7. customCrude material was purified
  8. washDesired product eluted with 5% ethyl acetate in hexane
  9. customto give
  10. concentrationafter concentration, 0.409 g of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(hydroxyamino)phenyl)carbamate

Sources & evidence

ORD record
ord-44c261a70fc043c5b3418e21f3538606
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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