Sodium Bicarbonate → 4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 409138Notes

Reaction equation

HRID 409138 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([CH3:11])[N:8](S(C3C=CC=CC=3)(=O)=O)[C:4]=2[N:5]=[CH:6][N:7]=1.CC([O-])(C)C.[K+].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([CH3:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 224844987-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 3354074-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 4-chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (10 g, 32.5. mmol, 1.0 eq) in THF (400 mL), t-BuOK (18.23 g, 163.0 mmol, 5 eq) was added and stirred at RT for 12 h. Sat. NaHCO3 (50 mL) was added and extracted with EtOAc. The organic layers were separated, dried and concentrated to afford 4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine as a brown solid (2.7 g, 50% in yield).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layers were separated
  3. customdried
  4. concentrationconcentrated
  5. customto afford

Sources & evidence

ORD record
ord-6acc4647fdfd4fddb6d3a9ea7291a78b
Source dataset
uspto-grants-2014_06
Patent number
US08759358B1

Reaction notes

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