Acetic Acid → 4-(1-Ethyl-propenyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1884350Notes

Reaction equation

HRID 1884350 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:22](O)([CH2:25][CH3:26])[CH2:23][CH3:24])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:6]=2[N:7]=1.S(=O)(=O)(O)O.C(O)(=O)C.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.[OH-].[Na+]>O>[CH2:25]([C:22]([C:4]1[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=3[CH3:19])[C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1)=[CH:23][CH3:24])[CH3:26]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 235057383-[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pentan-3-ol

Product 1

HCID 698922374-(1-Ethyl-propenyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidineYield 101.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pentan-3-ol (0.041 g, 0.122 mmol), concentrated sulfuric acid (0.055 g, 0.56 mmol) and acetic acid (0.136 g, 2.27 mmol) was heated to reflux for 1 hour, cooled, diluted with water, basified to pH10 with 2 N NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to dryness to give 43 mg of the title compound as a clear oil. The oil was purified through silica gel column chromatography to give 40 mg of the title compound as a white solid, mp 59-61° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-46e34791e23542c0aa504e80ad249709
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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