2,4,6-Trimethylphenol → HCID 57848881, compound

HRID 736327Notes

Reaction equation

HRID 736327 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[S:22][CH:21]=[C:20]([CH3:23])[C:18]=2[N:19]=1>C1COCC1.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[S:22][CH:21]=[C:20]([CH3:23])[C:18]=2[N:19]=1

Participants

6

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidine

Product 1

HCID 57848881HCID 57848881, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of NaH (16 mg, 0.4 mmol) in dry THF (2 mL) was added 2,4,6-trimethyl phenol and stirred at room temperature for 30 min under argon. The reaction mixture was added to a solution of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine (87 mg, 0.4 mmol) in dry THF (2 mL) at 0° C. and slowly warmed up to room temperature. After stirring the reaction for 2 h, the resulting mixture was 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 (2:1) to give the product as a white solid (136 mg, 90%):

Workup

  1. temperatureslowly warmed up to room temperature
  2. stirringAfter stirring
  3. customthe reaction for 2 h
  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 (2:1)

Sources & evidence

ORD record
ord-7513dd4ba4e842aa96ad460cf6790578
Source dataset
uspto-grants-2009_09
Patent number
US07595324B2

Reaction notes

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