Phosphorus oxychloride → HCID 86720527, compound

HRID 1755226Notes

Reaction equation

HRID 1755226 reaction equation
[CH:1]([C:4]1[NH:5][C:6](=O)[C:7]2[N:8]([CH:10]=[CH:11][CH:12]=2)[CH:9]=1)([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:6]1[C:7]2[N:8]([CH:10]=[CH:11][CH:12]=2)[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86720528HCID 86720528, compound

Product 1

HCID 86720527HCID 86720527, compoundYield 62%

Conditions

Temperature
70 °C

Procedure

3-isopropylpyrrolo[1,2-a]pyrazin-1(2H)-one from step b (1.6 g, 4.7 mmol) was combined with POCl3 (20 mL) and stirred at 70° C. for 20 minutes. POCl3 was removed under reduced pressure. The residue was taken up in DCM and washed twice with saturated sodium bicarbonate. Afterward the organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 5-10% MTBE/hexanes) to provide chloro-3-isopropylpyrrolo[1,2-a]pyrazine (1.09 g, 62% yield).

Workup

  1. customPOCl3 was removed under reduced pressure
  2. washwashed twice with saturated sodium bicarbonate
  3. dry with materialAfterward the organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, 5-10% MTBE/hexanes)

Sources & evidence

ORD record
ord-7fd2336c78aa458d9d95890dd8ffaea3
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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