Water → HCID 71239723, compound

HRID 1403236Notes

Reaction equation

HRID 1403236 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[CH2:20][CH3:21])=[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Br:27]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[CH2:20][CH3:21])=[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:9]=2)[C:5]([Br:27])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 70980634HCID 70980634, compound

Product 1

HCID 71239723HCID 71239723, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-ethylphenyl)-1H-pyrrole-3-carboxylate (450 mg, 1.21 mmol) in DMF (7.5 mL) was treated with N-bromosuccinimide (216 mg, 1.21 mmol). The mixture was stirred overnight at room temperature, then poured into water, extracted with EtOAc (2×30 mL). The separated organic phase was dried over sodium sulfate and the solvent evaporated. Crystallization from diethyl ether afforded the title compound (420 mg, 77%).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. dry with materialThe separated organic phase was dried over sodium sulfate
  3. customthe solvent evaporated
  4. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-6d54d44adbe2472582000dd9f924d2b1
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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