Phosphorus oxychloride → HCID 59312985, compound

HRID 2389801Notes

Reaction equation

HRID 2389801 reaction equation
[Br:1][C:2]1[N:6]2[C:7](O)=[N:8][C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[C:10]([Br:11])[C:5]2=[N:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[N:6]2[C:7]([Cl:23])=[N:8][C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[C:10]([Br:11])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate2×HCID 178517480HCID 178517480, compound

Product 1

HCID 59312985HCID 59312985, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

575 mg (1.3 mmol) of 3,8-dibromo-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-ol (Example 123A) are introduced into phosphoryl chloride (5 ml), 900 mg (4 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 12 h. The reaction mixture is slowly poured, while stirring vigorously, into saturated sodium bicarbonate solution, and solid sodium bicarbonate (approx. 3 g) is added until a pH of 10 is reached. The mixture is stirred for 10 min, ethyl acetate (100 ml) is added and shaken, and the organic phase is separated off, washed with water and dried over magnesium sulphate and concentrated in a rotary evaporator. The residue is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1). 480 mg (80% of theory) of the product are obtained.

Workup

  1. additionare added
  2. additionThe reaction mixture is slowly poured
  3. additionis added until a pH of 10
  4. stirringThe mixture is stirred for 10 min
  5. stirringshaken
  6. customthe organic phase is separated off
  7. washwashed with water
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated in a rotary evaporator
  10. customThe residue is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1)
  11. custom480 mg (80% of theory) of the product are obtained

Sources & evidence

ORD record
ord-293edb3570fb44c8b05911784a0cd890
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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