Iodine → 4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

HRID 2375813Notes

Reaction equation

HRID 2375813 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.[Li+].CC([N-]C(C)C)C.[I:28]I.O>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([I:28])[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

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 2724682Lithium diisopropylamideHCID 109463064-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]-pyrimidine (5.0 g, 0.017 mol) in THF (200 mL) under inert atmosphere, at −78° C., was added 2.0 M LDA solution (9.8 mL, 0.0195 mol) over a period of 15 min. After 1 h a solution of iodine (4.97 g, 0.0196 mol) in THF (50 mL) was added dropwise over a period of 15 min. The resulting solution was stirred for a further 3 h. Water (10 mL) was then added and the mixture allowed to reach r.t. The mixture was diluted with DCM (1 l), washed with brine (2×100 mL), dried and concentrated under reduced pressure. The resulting solid was triturated with MeCN to afford the 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine. 1H NMR (CDCl3, 400 MHz) 7.05 (1H, s), 7.50 (2H, t), 7.60 (1H, t), 8.20 (2H, d) and 8.65 (1H, br s).

Workup

  1. customto reach r.t
  2. washwashed with brine (2×100 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solid was triturated with MeCN

Sources & evidence

ORD record
ord-c84059d700734fa6a06040b6d5a800d8
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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