Potassium Carbonate → tert.-Butyl [6-(4-cyanophenyl)-5-(cyclobutylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidine-1(2H)-yl]acetate

HRID 421796Notes

Reaction equation

HRID 421796 reaction equation
[CH:1]1([C:5]([C:7]2[CH:8]([C:25]3[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=3)[NH:9][C:10](=[O:24])[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[C:12]=2[CH3:13])=[O:6])[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>CN(C)C=O>[C:29]([C:28]1[CH:27]=[CH:26][C:25]([CH:8]2[N:9]([CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:10](=[O:24])[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=3)[C:12]([CH3:13])=[C:7]2[C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])=[CH:32][CH:31]=1)#[N:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 59684872HCID 59684872, compound

Product 1

HCID 59684827tert.-Butyl [6-(4-cyanophenyl)-5-(cyclobutylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidine-1(2H)-yl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of 4-{5-(cyclobutylcarbonyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzonitrile (Example 20) (29 mg, 0.066 mmol) and potassium carbonate (16.4 mg, 0.12 mmol) in dimethylformamide (1 ml) is treated with tert.-butyl bromoacetate (14.2 mg, 0.073 mmol), and then stirred at room temperature overnight (16 h). The reaction solution is quenched with water (3 ml) and extracted with diethyl ether (2×5 ml). The combined organic phases are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated.

Workup

  1. customThe reaction solution is quenched with water (3 ml)
  2. extractionextracted with diethyl ether (2×5 ml)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f53655322afe4030a0525aa709724dd4
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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