Phosphorus oxychloride → HCID 18380174, compound

HRID 2299269Notes

Reaction equation

HRID 2299269 reaction equation
O[C:2]1[C:14]2[N:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:8]3=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:2]1[C:14]2[N:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:8]3=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424434HCID 178424434, compound

Product 1

HCID 18380174HCID 18380174, compound

Procedure

A solution of 4-Hydroxy-2-methyl-10-(2,4,6-trimethylphenyl)pyrido-[2′,3′:4,5]pyrrolo[1,2-a]pyrazine (220 mg) in phosphorus oxychloride (2 mL) is heated to 100° C. for 1 hour. The resulting dark tan solution is concentrated in vacuo, diluted with water, and neutralized by adding saturated sodium bicarbonate solution. The neutralized solution is extracted 3 times with dichloromethane and the combined extracts are dried (Na2SO4), filtered, concentrated, and chromatographed on silica gel (10 to 20% ethyl acetate in hexane) to give 120 mg of the title compound as a yellow foam: 1H nmr (400 MHz, CDCl3) d 2.03 (s, 5 H), 2.38 (s, 3 H), 2.69 (s, 3 H), 7.03 (s, 2 H) 7.25 (s, 1 H), 7.66 (d, 1 H), 8.70 (s, 1 H), 9.00 (d, 1 H).

Workup

  1. concentrationThe resulting dark tan solution is concentrated in vacuo
  2. additiondiluted with water
  3. additionby adding saturated sodium bicarbonate solution
  4. extractionThe neutralized solution is extracted 3 times with dichloromethane
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel (10 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5b4b70b10d934e968b6d1d449288adc1
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

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