N-bromobutanimide → 5-Bromo-6-phenylfuro[2,3-d]pyrimidine-4-amine

HRID 2189044Notes

Reaction equation

HRID 2189044 reaction equation
[C:1]1([C:7]2[O:16][C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][C:8]1[C:9]2[C:14]([NH2:15])=[N:13][CH:12]=[N:11][C:10]=2[O:16][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6965246-Phenylfuro[2,3-d]pyrimidin-4-amine

Product 1

HCID 594278295-Bromo-6-phenylfuro[2,3-d]pyrimidine-4-amineYield 78.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat 80 g (378.7 mmol) 6-phenylfuro[2,3-d]pyrimidine-4-amine in 770 ml carbon tetrachloride to 60° C. Add 84.3 g (473.4 mmol) N-bromosuccinimide, and stir the mixture overnight under reflux. After cooling, filter, mix the filter cake successively with dichloromethane and acetonitrile, and filter again. Then dry the filter cake under vacuum. 86 g of the target product (78.2% of theor.) is obtained.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. filtrationfilter
  4. additionmix the filter cake successively with dichloromethane and acetonitrile
  5. filtrationfilter again
  6. customThen dry the filter cake under vacuum

Sources & evidence

ORD record
ord-8e92fd1377cd4a1a9710c67575534cbc
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…