Bromine → HCID 58133724, compound

HRID 336898Notes

Reaction equation

HRID 336898 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11](=[O:31])[NH:10]2)=[C:5]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:4]=1)#[N:2].[Br:36]Br>C(Cl)(Cl)Cl>[Br:36][CH2:20][C:13]1[N:12]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[C:11](=[O:31])[NH:10][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[S:32]([CH3:35])(=[O:33])=[O:34])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 58133718HCID 58133718, compound

Product 1

HCID 58133724HCID 58133724, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

(rac)-Ethyl 4-[4-cyano-2-(methylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate (Example 115; 3.00 g, 5.62 mmol) was dissolved in chloroform (49.9 ml), and the solution was cooled to 0° C. on an ice bath. Bromine (987 mg, 6.18 mmol) was then added dropwise. Subsequently, the ice bath was removed and the reaction mixture was stirred at RT for 1 h. Sodium thiosulfate solution (50 ml) was then added, and the organic phase was separated off, dried over sodium sulfate and concentrated under reduced pressure. The residue was triturated with diethyl ether, and the solid was filtered off with suction and washed with diethyl ether. This gave 2.96 g (90% of theory) of the target compound as a yellow crystalline solid.

Workup

  1. customSubsequently, the ice bath was removed
  2. additionSodium thiosulfate solution (50 ml) was then added
  3. customthe organic phase was separated off
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe solid was filtered off with suction
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-3dfad86c24d44bad923d4f47788be998
Source dataset
uspto-grants-2014_11
Patent number
US08889700B2

Reaction notes

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