Phosphorus oxybromide → HCID 21946020, compound

HRID 2216980Notes

Reaction equation

HRID 2216980 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9](O)[CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.P(Br)(Br)([Br:25])=O>BrCBr>[Br:25][CH:9]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 81531DiisopropylethylamineHCID 21946010HCID 21946010, compound

Product 1

HCID 21946020HCID 21946020, compound

Reagents, catalysts & solvents 1

HCID 3024DibromomethaneSolvent

Procedure

(±)-1-(2,4-Dichloro-pyrimidin-5-yl)-2-methyl-propan-1-ol (0.18 g; 0.83 mmol) (from Example 11a supra) was combined with N,N-diisopropyl-ethylamine (0.37 mL; 2.10 mmol) (Aldrich) and a small volume of dibromomethane (50 μL) (Aldrich) to help solubilize the mixture. Only a small amount of material remained insoluble. Neat phosphorus oxybromide (0.22 g; 0.85 mmol) (Aldrich) was added in one portion. Reaction mixture was stirred for 10 minutes and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography (Biotage 12M) gave (±)-5-(1-bromo-2-methyl-propyl)-2,4-dichloro-pyrimidine as a colorless oil. (Yield 79.5 mg; 33.7%).

Workup

  1. customReaction mixture
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (Biotage 12M)

Sources & evidence

ORD record
ord-0065ed9206114f5cba91504e52eba4df
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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