Phosphorus oxychloride → ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate

HRID 7417

Reaction equation

HRID 7417 reaction equation
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[N:3]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418799HCID 178418799, compound

Product 1

HCID 21990788ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylateYield 477.4%

Conditions

Temperature
120 °C

Procedure

To ethyl 4-hydroxy-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (2.85 g, 10 mmol) was added phosphorus oxychloride (10 mL, 2 mmol) and the mixture was stirred at 120° C. for 15 h. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution (×3) and saturated brine (×1) and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give the title compound (2.9 g, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogencarbonate solution (×3) and saturated brine (×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b563b66a76d47b3b1470b157246b957
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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