Hydrochloric Acid → 6-Amino-5-[(6-hydroxy-2,5,7,8-tetramethyl-2-chromanylmethyl)amino]-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione

HRID 399424Notes

Reaction equation

HRID 399424 reaction equation
C([O:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:36])([C:17]([NH:19][C:20]1[C:21](=[O:35])[N:22]([CH3:34])[C:23](=[O:33])[N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:25]=1[NH2:26])=O)[CH2:9][CH2:8]2)(=O)C.Cl>C1COCC1>[NH2:26][C:25]1[N:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:23](=[O:33])[N:22]([CH3:34])[C:21](=[O:35])[C:20]=1[NH:19][CH2:17][C:10]1([CH3:36])[CH2:9][CH2:8][C:7]2[C:12](=[C:13]([CH3:16])[C:14]([CH3:15])=[C:5]([OH:4])[C:6]=2[CH3:37])[O:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 572790375-(6-Acetoxy-2.5,7,8-tetramethvlchroman-2-carboxamido)-6-amino-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione

Product 1

HCID 1317208806-Amino-5-[(6-hydroxy-2,5,7,8-tetramethyl-2-chromanylmethyl)amino]-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedioneYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 14 (64 mg, 1.0 mmol) was dissolved in THF (10 mL). To the resultant solution was added borane-methyl sulfide complex (10 M, 0.24 mL, 2.4 mmol). The resultant reaction mixture was refluxed for 5 h. To the resultant was added 1N hydrochloric acid (2.4 mL) under ice-cooling. The resultant mixture was refluxed for 2 h, followed by concentration under reduced pressure. The residue was extracted with dichloromethane after addition of 1N aqueous solution of sodium hydroxide. The organic layer was washed with 10% aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized by addition of ethyl acetate and ether to give the title compound (yield 35%).

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas refluxed for 5 h
  3. temperaturecooling
  4. concentrationfollowed by concentration under reduced pressure
  5. extractionThe residue was extracted with dichloromethane
  6. additionafter addition of 1N aqueous solution of sodium hydroxide
  7. washThe organic layer was washed with 10% aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized by addition of ethyl acetate and ether

Sources & evidence

ORD record
ord-706e3c1f043d4f1c82e5b7ec86c93210
Source dataset
uspto-grants-1998_10
Patent number
US05821247

Reaction notes

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