Potassium Bromide → HCID 19966732, compound

HRID 976229Notes

Reaction equation

HRID 976229 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14][S:15]([NH:18][N:19]2[CH:23]=[CH:22][CH:21]=[CH:20]2)(=[O:17])=[O:16])=[O:13])[N:4]=1.[K+].[Br-:25]>O1CCCC1>[Br:25][C:20]1[N:19]([NH:18][S:15]([NH:14][C:12]([NH:11][C:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=2)=[O:13])(=[O:16])=[O:17])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 19966748HCID 19966748, compound

Product 1

HCID 19966732HCID 19966732, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4,6-dimethoxypyrimidin-2-yl)-N'-{[(1H-pyrrol-1-yl)amino]sulfonyl}urea (I-53; 0.164 g; 0.48 mM) synthesized according to synthesis Example 1 at room temperature was dissolved in 10 ml of tetrahydrofuran. To the solution was added under cooling with ice-water N-bromosuccinimide (0.085 g; 0.48mM). After cooled for a short period of time, the mixture was stirred at room temperature for 3 hours. The solvent in the reaction mixture was then distilled away and the resultant residue was purified with column chromatography on silica gel to obtain the target product. White solid; m.p. 157° C.; Yield 0.095 g (47.5%) IR (KBr cm-1): 3320 3132 1716 1614 1582 1454 1364 1170 NMR(CDCl3, δ): 3.7(6H,s:pyrimidine ring OCH3 ×2) 5.6(1H,s:pyrimidine ring H) 6.0(2H,m:pyrrole ring C3 and C4) 6.7~6.9(1H,m:pyrrole ring C5) 8.5(1H,bs:NH) 12.5(1H,bs:NH)

Workup

  1. customaccording to synthesis Example 1 at room temperature
  2. additionTo the solution was added
  3. temperatureAfter cooled for a short period of time
  4. distillationThe solvent in the reaction mixture was then distilled away
  5. customthe resultant residue was purified with column chromatography on silica gel
  6. customto obtain the target product

Sources & evidence

ORD record
ord-0c866387a1c7447ab36905a862bc132f
Source dataset
uspto-grants-1997_03
Patent number
US05612287

Reaction notes

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