Phosphorus oxychloride → HCID 86595016, compound

HRID 2121586Notes

Reaction equation

HRID 2121586 reaction equation
[CH3:1][C:2]1[N:3]=[C:4](O)[C:5]2[N:13]3[C:8]([C:9]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=4[CH3:22])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:23]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:4]1[C:5]2[N:13]3[C:8]([C:9]([C:14]4[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=4[CH3:20])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:23]=[C:2]([CH3:1])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424532HCID 178424532, compound

Product 1

HCID 86595016HCID 86595016, compound

Procedure

Heat at 100° C. for 2 h a solution of 2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indolizin-4-ol (120 mg) in phosphorus oxychloride (2 mL), cool to ambient temperature, and concentrate in vacuo. Partition the residue into ice water and CH2Cl2. Extract the aqueous phase twice with CH2Cl2 and wash the combined organic extracts with a saturated NaHCO3 solution. Dry the solution over Na2SO4, filter, and concentrate in vacuo. Purify the dark residue by column chromatography on silica gel (eluent: 10% to 20% EtOAc in hexane) to obtain the title compound as a greenish yellow foam: 1H NMR (400 MHz, CDCl3) δ 1.99 (s, 6H), 2.38 (s, 3H), 2.79 (s, 3H), 6.80 (m, 1H), 7.00 (s, 2H), 7.19 (m, 2H), 9.27 (d, 1H).

Workup

  1. concentrationconcentrate in vacuo
  2. customPartition the residue into ice water and CH2Cl2
  3. extractionExtract the aqueous phase twice with CH2Cl2
  4. washwash the combined organic extracts with a saturated NaHCO3 solution
  5. dry with materialDry the solution over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the dark residue by column chromatography on silica gel (eluent: 10% to 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-beba1cc35f6c4f3c94ded4dbf0ec06ba
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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