Pyridine → 5-(6-Acetoxy-2.5,7,8-tetramethvlchroman-2-carboxamido)-6-amino-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione

HRID 399423Notes

Reaction equation

HRID 399423 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[C:3]=1[NH:17][C:18]([C:20]1([CH3:34])[CH2:29][CH2:28][C:27]2[C:22](=[C:23]([CH3:33])[C:24]([CH3:32])=[C:25]([OH:31])[C:26]=2[CH3:30])[O:21]1)=[O:19].N1C=CC=CC=1.[C:41](OC(=O)C)(=[O:43])[CH3:42]>ClCCl>[C:41]([O:31][C:25]1[C:26]([CH3:30])=[C:27]2[C:22](=[C:23]([CH3:33])[C:24]=1[CH3:32])[O:21][C:20]([CH3:34])([C:18]([NH:17][C:3]1[C:4](=[O:16])[N:5]([CH3:15])[C:6](=[O:14])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]=1[NH2:1])=[O:19])[CH2:29][CH2:28]2)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9825688HCID 9825688, compound

Product 1

HCID 572790375-(6-Acetoxy-2.5,7,8-tetramethvlchroman-2-carboxamido)-6-amino-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedioneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 1 (1.77 g, 3.80 mmol) and pyridine (0.154 mL, 1.90 mmol) were dissolved in dichloromethane (30 mL). To the resultant solution was added dropwise acetic anhydride (0.714 mL, 7.60 mmol) under ice cooling. The resultant reaction mixture was stirred overnight at room temperature, washed with 1N hydrochloric acid and 10% aqueous solution of sodium chloride successively, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was suspended in ethyl acetate and filtered to give the title compound (yield 87%).

Workup

  1. customThe resultant reaction mixture
  2. washwashed with 1N hydrochloric acid and 10% aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c9b20a5e69464fa0a5a66a00e811cefa
Source dataset
uspto-grants-1998_10
Patent number
US05821247

Reaction notes

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