Acetic Acid → HCID 178424583, compound

HRID 2183549Notes

Reaction equation

HRID 2183549 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH3:15])=[CH:5][N:4]([CH3:16])[C:3]=1[C:17]#[N:18].[C:19](OC(=O)C)(=O)[CH3:20].C(O)(=[O:28])C>>[CH3:19][C:20]1[N:18]=[C:17]([OH:28])[C:3]2[N:4]([CH3:16])[CH:5]=[C:6]([C:7]3[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=3[CH3:15])[C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 224744433-amino-1-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole-2-carbonitrile

Product 1

HCID 178424583HCID 178424583, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 3-amino-1-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole-2-carbonitrile (0.4 mmol) and acetic anhydride (0.043 ml) in acetic acid (0.01 ml) was heated at reflux untill all the starting material was consumed. The reaction mixture was concentrated to dryness. The residue was quenched with water and extracted with ethyl acetate. The organic extracts was washed with brine and concentrated to dryness. The residue was suspended in 0.5 ml of 85% phosphoric acid and heated at 130° C. for 1 hour. The mixture was cooled and poured into ice-water, stirred until solid formed. The solid was filtered to give 2,5-dimethyl-7-(2,4,6-trimethylphenyl)-5H-pyrrolo[3,2-d]pyrimidin-4-ol. The alternative way for the work up is via extraction technique. The ice water was extracted with chloroform. The organic layer was dried and concentrated to dryness to give the desired product.

Workup

  1. temperaturewas heated
  2. temperatureat reflux untill all the starting material
  3. customwas consumed
  4. concentrationThe reaction mixture was concentrated to dryness
  5. customThe residue was quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic extracts was washed with brine
  8. concentrationconcentrated to dryness
  9. temperatureThe mixture was cooled
  10. additionpoured into ice-water
  11. customformed
  12. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-46a0cd66022e43aa811d1026fabe240d
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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