Bromine → HCID 22084576, compound

HRID 398037Notes

Reaction equation

HRID 398037 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 •l, 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-2b73ce5107c742fe9f768b0c2c42282e
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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