Potassium Carbonate → Acetic acid 2-[5-acetyl-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrimidine-2-ylsulfanyl]-ethyl ester

HRID 1921141Notes

Reaction equation

HRID 1921141 reaction equation
[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:14]([C:17]1[CH:18]([C:35]2[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=2)[NH:19][C:20](=[S:34])[N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:22]=1[CH3:23])(=[O:16])[CH3:15]>CN(C=O)C>[C:14]([C:17]1[CH:18]([C:35]2[CH:36]=[CH:37][C:38]([C:39]#[N:40])=[CH:41][CH:42]=2)[N:19]=[C:20]([S:34][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=2)[C:22]=1[CH3:23])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 115968194-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Product 1

HCID 57762457Acetic acid 2-[5-acetyl-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrimidine-2-ylsulfanyl]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromoethyl acetate (37.6 mg, 0.23 mmol) in 500 μl DMF are added potassium carbonate (82.9 mg, 0.6 mmol) and 4-{5-acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile (Example 1; 62.3 mg, 0.15 mmol). The reaction mixture is shaken for 15 hours, filtered and purified by preparative HPLC (column: Nucleosil 100-5 C 18 Nautilus 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% formic acid; flow rate: 25 ml/min; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; wavelength: 220 nm; injection volume: approx. 550 μl; number of injections: 1). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC (column: Nucleosil 100-5 C 18 Nautilus 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% formic acid; flow rate: 25 ml/min; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; wavelength: 220 nm; injection volume: approx. 550 μl; number of injections: 1)
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a45aa35654a2498ab82ddf35addc7868
Source dataset
uspto-grants-2012_05
Patent number
US08173665B2

Reaction notes

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