Water → HCID 71240059, compound

HRID 1403232Notes

Reaction equation

HRID 1403232 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([NH2:23])=[O:22])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[I:24]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([NH2:23])=[O:22])[C:9]=2[I:24])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 57659335HCID 57659335, compound

Product 1

HCID 71240059HCID 71240059, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2-Amino-pyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxamide (1.1 g, 3.36 mmol) in dry DMF (6 mL) was treated with solid N-iodosuccinimide (830 mg, 3.69 mmol), stirred at room temperature for 4.5 h and poured into iced water (150 mL). The solid was then filtered with suction, washed thoroughly with water, dried in an oven under vacuum at 50° C. and purified by flash chromatography over silica gel (DCM/MeOH/7 N NH3 in MeOH 95/5/0.5) to afford the title compound (654 mg, 43%).

Workup

  1. filtrationThe solid was then filtered with suction
  2. washwashed thoroughly with water
  3. customdried in an oven under vacuum at 50° C.
  4. custompurified by flash chromatography over silica gel (DCM/MeOH/7 N NH3 in MeOH 95/5/0.5)

Sources & evidence

ORD record
ord-349185bcdacc4df199f63a41c4321241
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…