Phosphorus tribromide → HCID 178496187, compound

HRID 2197453Notes

Reaction equation

HRID 2197453 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][N:7]1[C:15]([OH:16])=[N:14][C:13]2[C:8]1=[N:9][C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[N:11][C:12]=2[NH2:17].P(Br)(Br)[Br:27]>C1COCC1>[Br:27][CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][N:7]1[C:15]([OH:16])=[N:14][C:13]2[C:8]1=[N:9][C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[N:11][C:12]=2[NH2:17]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178496189HCID 178496189, compound

Product 1

HCID 178496187HCID 178496187, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound (8) (51.4 mg, 0.148 mmol) in THF (2 mL) was added phosphorus tribromide (0.2 mL). The reaction mixture was allowed to stir at room temperature for 5 minutes then quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were dried over NaSO3 and evaporated to give Compound (9) as a white solid. The crude mixture was used in the next step without further purification. The identity of the product was verified by LCMS. LCMS: m/z for C16H19N5O4++H observed 346.1 at 1.69 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O. LCMS: m/z for C16H18BrN5O3++H observed 408.0 and 410.1 at 2.03 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Workup

  1. customthen quenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over NaSO3
  4. customevaporated

Sources & evidence

ORD record
ord-3c04de0f0ab042f5abaf07e5dac091a1
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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