2,4,6-Trimethylphenol → 2-Chloro-4-(mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 1805872Notes

Reaction equation

HRID 1805872 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[OH:12].[Cl:13][C:14]1[N:15]=[C:16](Cl)[C:17]2[N:22]([CH3:23])[CH:21]=[CH:20][C:18]=2[N:19]=1>CN1C(=O)CCC1.O>[Cl:13][C:14]1[N:15]=[C:16]([O:12][C:5]2[C:6]([CH3:11])=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=2[CH3:3])[C:17]2[N:22]([CH3:23])[CH:21]=[CH:20][C:18]=2[N:19]=1

Participants

6

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 147277632,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidine

Product 1

HCID 576936612-Chloro-4-(mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidineYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a stirred suspension of NaH (8.9 mg, 0.22 mmol) in dry NMP (1.0 mL) was added 2,4,6-trimethyl phenol (30.2 mg, 0.22 mmol) and stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 2,4-dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (44.6 mg, 0.22 mmol) in dry NMP (1.0 mL) and heated at 90° C. for 16 h. After completion of the reaction, the resulting mixture was cooled, diluted with water and washed with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (5:1-2:1), to give the product as a light yellow solid (52.7 mg, 80%).

Workup

  1. temperatureheated at 90° C. for 16 h
  2. customAfter completion of the reaction
  3. temperaturethe resulting mixture was cooled
  4. washwashed with EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography
  10. washeluting with hexanes/ethyl acetate (5:1-2:1)

Sources & evidence

ORD record
ord-3780e46649354737b5380021f0c46cbe
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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