Trifluoroacetic acid → HCID 178433458, compound

HRID 1798828Notes

Reaction equation

HRID 1798828 reaction equation
COC1C=CC(C[O:8][C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]#[N:17])[CH:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]#[N:17])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58128545HCID 58128545, compound

Product 1

HCID 178433458HCID 178433458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 6-[(4-methoxybenzyl)oxy]-2-methylpyrimidine-4-carbonitrile from step 2 of this example (2.8 g, 11 mmol) was dissolved in DCM (9.1 mL) and TFA (1.8 mL) was added via syringe drop-wise. The reaction was allowed to proceed 10 min. at room temperature and was concentrated to near dryness, without heating, under vacuum. The residue was dissolved in DCM (10 mL), and saturated NaHCO3 solution (aq, 5 mL) was added to adjust pH to ˜7. Acetic acid (1 mL) was then added to the solution to adjust pH to ˜4 and the mixture was concentrated to dryness i. vac. The residue was purified by chromatography on silica gel using gradient elution: starting at 30% ethyl acetate/hexane, then switching to 5% methanol/DCM to yield the titled compound as a white solid. LC-MS (M+1): 136.16.

Workup

  1. concentrationwas concentrated
  2. temperaturewithout heating, under vacuum
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. additionsaturated NaHCO3 solution (aq, 5 mL) was added
  5. additionAcetic acid (1 mL) was then added to the solution
  6. concentrationthe mixture was concentrated to dryness i
  7. customThe residue was purified by chromatography on silica gel using gradient elution

Sources & evidence

ORD record
ord-02e113f00a6840c4b9e30b4353474256
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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