Methyl iodide → 7-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 2207521Notes

Reaction equation

HRID 2207521 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:20]N(CCN(C)C)C.[Li]CCCC.CI>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([CH3:20])[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 109463064-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 224844987-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (3 g, 12.6 mmol, 1.0 eq) and TMEDA (3.0 mL, 18.9 mmol, 1.5 eq) in THF (120 mL) at −78° C. was added n-BuLi (7.5 mL, 18.9 mmol, 1.5 eq). After 3 min, CH3I (3.7 mL, 59.2 mmol, 4.7 eq) was added. After 3 h, the reaction mixture was warmed to RT over 1 h. The reaction was quenched by addition of sat NH4Cl (10 mL). EtOAc (200 mL) and water (100 mL) was added. The organic layer was separated, dried and concentrated to afford 4-chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine as a brown solid (6.7 g, 90% in yield).

Workup

  1. waitAfter 3 h
  2. customThe reaction was quenched by addition of sat NH4Cl (10 mL)
  3. additionEtOAc (200 mL) and water (100 mL) was added
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto afford

Sources & evidence

ORD record
ord-f6b29a567e3045e5bf851e66aa2d8964
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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