Hydrochloric Acid → HCID 57593275, compound

HRID 1785297Notes

Reaction equation

HRID 1785297 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]#[CH:11])[C:5]([C:12]([F:15])([F:14])[F:13])=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][NH:22]C(=O)C(F)(F)F)=[CH:19][CH:18]=1.Cl.ClCCl.CO>CO>[NH2:22][CH2:21][C:20]1[CH:29]=[CH:30][C:17]([NH:16][C:2]2[N:7]=[C:6]([NH:8][CH2:9][C:10]#[CH:11])[C:5]([C:12]([F:15])([F:14])[F:13])=[CH:4][N:3]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14298718HCID 14298718, compoundHCID 21226129Dichloromethane methanolHCID 58727636HCID 58727636, compound

Product 1

HCID 57593275HCID 57593275, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-chloro-4-(prop-2-ynylamino)-5-trifluoromethyl-pyrimidine (235 mg), N-(4-aminobenzyl)-2,2,2-trifluoro-acetamide (410 mg) and hydrochloric acid (37% in water, 0.2 mL) in methanol (5 mL) was refluxed for 1 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, the aqueous phase extracted with ethyl acetate, the combined organic phases dried (Na2SO4), concentrated, filtered through silica using dichloromethane/methanol, and the filtrate evaporated. To a solution of the residue in methanol (9 mL), tetrahydrofuran (9 mL) and diethyl ether (4-5 mL) was added lithium hydroxide (150 mg) and the mixture was refluxed for 6 h, after which it was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with additional ethyl acetate, the combined organic phases dried (Na2SO4) and evaporated, which gave, after chromatography on silica using dichloromethane/methanol, the title compound (120 mg).

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. dry with materialthe combined organic phases dried (Na2SO4)
  5. concentrationconcentrated
  6. filtrationfiltered through silica
  7. customthe filtrate evaporated
  8. additionTo a solution of the residue in methanol (9 mL), tetrahydrofuran (9 mL) and diethyl ether (4-5 mL) was added lithium hydroxide (150 mg)
  9. temperaturethe mixture was refluxed for 6 h
  10. customafter which it was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  11. extractionThe aqueous phase was extracted with additional ethyl acetate
  12. dry with materialthe combined organic phases dried (Na2SO4)
  13. customevaporated
  14. customwhich gave

Sources & evidence

ORD record
ord-0f6531e17c464e9e8521ddfd18dbd2c7
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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