Trifluoroacetic acid → HCID 10173378, compound

HRID 897399Notes

Reaction equation

HRID 897399 reaction equation
[CH3:1][C:2]([NH:10][C:11]1[N:16]=[C:15]([NH:17][NH2:18])[C:14]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:13]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:12]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[CH3:32]OC(OC)OC.FC(F)(F)C(O)=O>C(Cl)Cl>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:14]2[C:15]3[N:16]([CH:32]=[N:18][N:17]=3)[C:11]([NH:10][C:2]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)([CH3:1])[CH3:3])=[N:12][C:13]=2[C:26]2[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 22346624HCID 22346624, compound

Product 1

HCID 10173378HCID 10173378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((1-methyl-1-phenylethyl)amino)-4-hydrazino-5-(4-fluorophenyl)-6-(4-pyridyl)pyrimidine (95.1 mg, 0.23 mmol) was combined with trimethylorthoformate (58.4 mg, 0.54 mmol) in CH2Cl2 (ca. 5 mL). Trifluoroacetic acid (62.6 mg, 0.54 mmol) was added and the solution was maintained for 1 h. The reaction mixture was washed with saturated NaHCO3. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography to provide the product as an off-white solid; MS m/z (M+H)+ 425; C25H21FN6 requir. 424.5.

Workup

  1. temperaturethe solution was maintained for 1 h
  2. washThe reaction mixture was washed with saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-de6aa9c0bb294e96b30a5a1ceedaaeec
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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