Phosphorus oxychloride → HCID 18380170, compound

HRID 2299266Notes

Reaction equation

HRID 2299266 reaction equation
O[C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]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])[N:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]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])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424435HCID 178424435, compound

Product 1

HCID 18380170HCID 18380170, compound

Procedure

A solution of 4-hydroxy-2-methyl-10-(2,4,6-trimethylphenyl)pyrimido-[4,5-b]indolizine (120 mg) in phosphorus oxychloride (2 mL) is heated at 100° C. for 2 hours, cooled to room temperature, and concentrated in vacuo. The residue is partitioned into ice water and dichloromethane. The aqueous phase is separated and extracted twice with dichloromethane. The combined organic extracts are washed with a saturated sodium bicarbonate solution and subsequently dried (Na2SO4), filtered, and concentrated in vacuo. The resulting dark residue is chromatographed on silica gel (10% to 20% ethyl acetate in hexane) to give 54 mg of the title compound as a greenish yellow foam: 1H nmr (400 MHz, CDCl3) d 1.99 (s, 6 H), 2.38 (s, 3 H), 2.79 (s, 3 H), 6.80 (m, 1 H), 7.00 (s, 2 H), 7.19 (m, 2 H), 9.27 (d, 1 H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is partitioned into ice water and dichloromethane
  3. customThe aqueous phase is separated
  4. extractionextracted twice with dichloromethane
  5. washThe combined organic extracts are washed with a saturated sodium bicarbonate solution
  6. dry with materialsubsequently dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting dark residue is chromatographed on silica gel (10% to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-44a23a53e46347fb8af00374a9954827
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

Loading…