N-Iodosuccinimide → 5-Iodo-7-[1-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 82276Notes

Reaction equation

HRID 82276 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[CH:20][C:15]=3[CH:14]=[CH:13]2)[CH2:11][CH2:10]1.[I:21]N1C(=O)CCC1=O>CN(C=O)C>[I:21][C:14]1[C:15]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[N:12]([C:9]2([CH2:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH2:11][CH2:10]2)[CH:13]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 70817177HCID 70817177, compound

Product 1

HCID 708172755-Iodo-7-[1-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidineYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-[1-(Tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidine (Preparation 248, 390 mg, 1.43 mmol) in DMF (8 mL) was added N-iodosuccinimide (481.5 mg, 2.14 mmol) and stirred at room temperature for 4 hours. The reaction mixture was quenched with water (8 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with water (5×15 mL), brine (10 mL), dried over sodium sulphate and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 99:1) to afford the title compound as a solid in 79% yield, 450 mg.

Workup

  1. customThe reaction mixture was quenched with water (8 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layer was washed with water (5×15 mL), brine (10 mL)
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 99:1)

Sources & evidence

ORD record
ord-2f69f74a831c4ef8bdf705f5af7def84
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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