Hydrochloric Acid → HCID 58016833, compound

HRID 1926870Notes

Reaction equation

HRID 1926870 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:10]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:15][C:11]=2[N:12]=[CH:13][N:14]=1)C.Cl.O>CC(C)=O>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:10]3[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH:4]=[O:3])=[N:14][CH:13]=[N:12][C:11]=3[O:15][C:16]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58016847HCID 58016847, compound

Product 1

HCID 58016833HCID 58016833, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 640 mg (1.39 mmol) N-(4,4-diethoxybutyl)-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine-4-amine in 5 ml acetone and, at RT, add 1 ml 1 N hydrochloric acid. After 1 h, add the reaction mixture to water and extract three times with dichloromethane. Combine the organic phases and wash with buffer solution (pH 7) and saturated sodium chloride solution, dry over magnesium sulphate and concentrate under vacuum. Purify the raw product by chromatography on silica gel (solvent: dichloromethane/ethyl acetate 2:1). 191 mg (35.6% of theor.) of the target compound is obtained.

Workup

  1. extractionextract three times with dichloromethane
  2. washwash with buffer solution (pH 7) and saturated sodium chloride solution
  3. dry with materialdry over magnesium sulphate
  4. concentrationconcentrate under vacuum
  5. customPurify the raw product by chromatography on silica gel (solvent: dichloromethane/ethyl acetate 2:1)
  6. custom191 mg (35.6% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-a658b9a5c86c4e3cb5e001999186049b
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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