Phosphorus oxychloride → HCID 59312973, compound

HRID 2389802Notes

Reaction equation

HRID 2389802 reaction equation
[Cl: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]([Cl: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>[Cl: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]([Cl:11])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate2×HCID 178517486HCID 178517486, compound

Product 1

HCID 59312973HCID 59312973, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

200 mg (0.4 mmol) of 3,8-dichloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-ol (Example 124A) are introduced into phosphoryl chloride (2 ml), 300 mg (1.3 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 12 h. The reaction mixture is slowly added, with vigorous stirring, to saturated sodium bicarbonate solution, and solid sodium bicarbonate (approx. 1.5 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). 150 mg (94% of theory) of the product are obtained.

Workup

  1. additionare added
  2. additionis added until a pH of 10
  3. stirringThe mixture is stirred for 10 min
  4. stirringshaken
  5. customthe organic phase is separated off
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in a rotary evaporator
  9. customThe residue is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1)
  10. custom150 mg (94% of theory) of the product are obtained

Sources & evidence

ORD record
ord-bc1e1a8e9446498b87aa99df763209d2
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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