N-bromobutanimide → HCID 58296328, compound

HRID 390062Notes

Reaction equation

HRID 390062 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[C:20](=[O:21])[NH:19][CH:18]=[CH:17][C:11]=3[N:12]=[C:13]([S:15][CH3:16])[N:14]=2)[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:29])C(=O)C1>CN(C)C=O>[Br:29][C:17]1[C:11]2[N:12]=[C:13]([S:15][CH3:16])[N:14]=[C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[C:10]=2[C:20](=[O:21])[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58296312HCID 58296312, compound

Product 1

HCID 58296328HCID 58296328, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(3-methylphenyl)amino]-2-(methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one (500 mg, 1.676 mmol) was dissolved into N,N-Dimethylformamide (DMF) (8 mL) and NBS (298 mg, 1.676 mmol) was added. The reaction mixture was stirred at rt for 2 h. It was quenched with water (12 mL) and EtOAc (5 mL) was added. The mixture was filtered to collect the precipitate, which was further dried under high vacuum to give 470 mg of crude product (83% pure based on LC-MS).

Workup

  1. additionwas added
  2. customIt was quenched with water (12 mL) and EtOAc (5 mL)
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. customto collect the precipitate, which
  6. customwas further dried under high vacuum

Sources & evidence

ORD record
ord-73345933f8024366b423f3153a7150da
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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