3,5-Dimethyl-4-hydroxybenzonitrile → HCID 57848883, compound

HRID 2188991Notes

Reaction equation

HRID 2188991 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:11]([CH3:12])=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[CH3:13].[Cl:14][C:15]1[N:16]=[C:17](Cl)[C:18]2[S:23][CH:22]=[CH:21][C:19]=2[N:20]=1>CN1C(=O)CCC1.O>[Cl:14][C:15]1[N:16]=[C:17]([O:3][C:4]2[C:5]([CH3:13])=[CH:6][C:7]([C:8]#[N:9])=[CH:10][C:11]=2[CH3:12])[C:18]2[S:23][CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

6

Reactant 3

HCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 24758Sodium hydrideHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 57848883HCID 57848883, compoundYield 315%

Reagents, catalysts & solvents 2

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

Procedure

A stirred suspension of NaH (29.7 mg, 0.74 mmol) in dry NMP (3.5 mL) was added 4-hydroxy-3,5-dimethylbenzonitrile (108.2 mg, 0.74 mmol) and stirred at room temperature for 30 min under Argon. The reaction mixture was added to a solution of 2,4-dichlorothieno[3,2-d]pyrimidine (39.6 mg, 0.19 mmol) in dry NMP (4 mL) and heated at 50° C. for 5 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 (4:1) to give the product as a white solid (189 mg, 81%):

Workup

  1. temperatureheated at 50° C. for 5 h
  2. washwashed with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography
  8. washeluting with hexanes/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-855b113d5c7540d1838a4b4153b421f3
Source dataset
uspto-grants-2012_12
Patent number
US08324223B2

Reaction notes

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