Trifluoroacetic anhydride → HCID 59380350, compound

HRID 2353314Notes

Reaction equation

HRID 2353314 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([NH:13][CH2:14][CH:15](OC)OC)[N:5]=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[N:3]=1.FC(F)(F)C(O)=O.ClCCl.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[N:5]2[CH:15]=[CH:14][N:13]=[C:6]2[C:7]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 57542080HCID 57542080, compound

Product 1

HCID 59380350HCID 59380350, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methyl [4-chloro-6-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (100 mg, 0.19 mmol) was treated with 50% trifluoroacetic acid/dichloromethane (5 mL) at room temperature overnight. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with aq NaHCO3 and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was dissolved in dichloromethane (5 mL). To the solution was added trifluoroacetic anhydride (0.053 mL, 0.38 mmol). The mixture was stirred at room temperature for 3 hours. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with aq NaHCO3 and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative TLC (silica gel, chloroform:ethanol, 19/1) to give methyl [7-chloro-5-(4-nitrobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (22 mg, 25%) as a colorless film.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with aq NaHCO3 and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in dichloromethane (5 mL)
  7. extractionextracted with dichloromethane
  8. washThe extracts were washed with aq NaHCO3 and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product was purified by preparative TLC (silica gel, chloroform:ethanol, 19/1)

Sources & evidence

ORD record
ord-26148577e27e4eafb0f3f6d5ec572c6a
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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