Bromine → HCID 22084576, compound

HRID 2188471Notes

Reaction equation

HRID 2188471 reaction equation
[Br:1]Br.[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]([Br:1])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 59897304HCID 59897304, compound

Product 1

HCID 22084576HCID 22084576, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (787 μl, 15.28 mmol) was added to a stirring solution of 2-(((S)-2-amino-3-phenylpropyl)-amino)-4-(4-pyridyl)-pyrimidine (2.33 g, 7.64 mmol) in chloroform (25 ml). Stirring was continued for 2 d. The mixture was partitioned between dichloromethane and aqueous sodium hydrogencarbonate. The organic solution was washed with brine, dried and evaporated. The resultant product was purified on a column of silica gel (dichloromethane-methanol-conc. ammonium hydroxide=92:8:0.6). MS (m/z): 384.0, 386.0 (M+H)+; C18H18BrN5 requir. 384.3.

Workup

  1. customThe mixture was partitioned between dichloromethane and aqueous sodium hydrogencarbonate
  2. washThe organic solution was washed with brine
  3. customdried
  4. customevaporated
  5. customThe resultant product was purified on a column of silica gel (dichloromethane-methanol-conc. ammonium hydroxide=92:8:0.6)

Sources & evidence

ORD record
ord-af6bc6906d914e92998fc2443f53e2ee
Source dataset
uspto-grants-2002_06
Patent number
US06410729B1

Reaction notes

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