N-bromobutanimide → 5-Bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

HRID 1355818Notes

Reaction equation

HRID 1355818 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([S:12][CH3:13])[N:9]=[C:8]([NH2:14])[N:7]=1.[Br:15]N1C(=O)CCC1=O>C(O)(=O)C>[Br:15][C:11]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:7][C:8]([NH2:14])=[N:9][C:10]=1[S:12][CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 185076524-Furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 185075225-Bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamineYield 34.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 197 mg (0.95 mmol) 4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine in 15 ml acetic acid was added 178 mg (1.00 mmol) N-bromosuccinimide and stirring continued at room temperature for 48 h. The reaction mixture was then concentrated in vacuo and the residue partitioned between ether and water. The organic phase was dried over, sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/2) followed by trituration in ether/hexane then afforded 93 mg (34%) 5-bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as a yellow crystalline solid. EI-MS m/e (%): 287 (M{81Br}+, 44), 285 (M{79Br}+, 42), 206 ([M—Br]+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between ether and water
  3. dry with materialThe organic phase was dried over, sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa080306a71b4f81bd3b312fd8af2031
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…