Trifluoroacetic acid → 4-Amino-6-(4-nitrophenoxy)pyrimidine

HRID 2069146Notes

Reaction equation

HRID 2069146 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:11]1[CH:10]=[C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:24][CH:23]=2)[N:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 70881437tert-Butyl 6-(4-nitrophenoxy)pyrimidin-4-ylcarbamate

Product 1

HCID 229369424-Amino-6-(4-nitrophenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 6-(4-nitrophenoxy)pyrimidin-4-ylcarbamate (1.22 g, 85% purity, 3.12 mmol) in DCM (12.0 mL) was added TFA (1.4 mL, 18.4 mmol) and the reaction mixture stirred at RT for 1 hr. An additional aliquot of TFA (0.70 mL) was added and the mixture was kept at RT for 15 hr and was then evaporated in vacuo. The residue was partitioned between EtOAc (50 mL) and saturated aq NaHCO3 solution (50 mL) and the organic layer was separated and washed with brine (25 mL) and then dried (MgSO4). Evaporation of the volatiles in vacuo the title compound as a yellow solid (0.66 g, 89%); Rt 1.38 min (Method 2); m/z 233 (M−H)+ (ES+).

Workup

  1. waitthe mixture was kept at RT for 15 hr
  2. customwas then evaporated in vacuo
  3. customThe residue was partitioned between EtOAc (50 mL) and saturated aq NaHCO3 solution (50 mL)
  4. customthe organic layer was separated
  5. washwashed with brine (25 mL)
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the volatiles in vacuo the title compound as a yellow solid (0.66 g, 89%)

Sources & evidence

ORD record
ord-fd4aa241654d4ac6bf70acf215eef86d
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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