N-Iodosuccinimide → HCID 89613588, compound

HRID 882185Notes

Reaction equation

HRID 882185 reaction equation
[C:1]1([C:7]2[C:8]3[CH:15]=[CH:14][NH:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([I:23])C(=O)C1>CN(C=O)C>[I:23][C:15]1[C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12][CH:11]=[N:10][C:9]=2[NH:13][CH:14]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 45483929HCID 45483929, compound

Product 1

HCID 89613588HCID 89613588, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-phenyl-7H-pyrrolo[2,3-d]pyrimidine (5.28 g, 27.0 mmol) in DMF (100 mL) was added NIS (6.57 g, 29.2 mmol). The reaction was stirred at room temperature for 1.5 hours. The reaction mixture was quenched with water (150 mL) and the resulting precipitated product was filtered and washed with water. The filtrate cake was dried under vacuum to afford 5-iodo-4-phenyl-7H-pyrrolo[2,3-d]pyrimidine as a yellow solid. LRMS (ESI) calcd for C12H8IN3 [M]+: 321, found 321. 1H NMR (600 MHz, DMSO-D6) δ 12.71 (s, 1H), 8.83 (s, 1H), 7.87 (d, J=2.45 Hz, 1H), 7.68 (t, J 1.45 Hz, 1H), 7.67 (d, J=3.42 Hz, 1H), 7.54 (d, J=1.96 Hz, 2H), 7.53 (t, J=1.46 Hz, 1H).

Workup

  1. customThe reaction mixture was quenched with water (150 mL)
  2. customthe resulting precipitated product
  3. filtrationwas filtered
  4. washwashed with water
  5. customThe filtrate cake was dried under vacuum

Sources & evidence

ORD record
ord-dd7a763b47364afabf0f35f772c7eede
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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