Dimethylformamide → HCID 178476583, compound

HRID 230288Notes

Reaction equation

HRID 230288 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](C2C=CC(C#N)=CC=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].C[N:44]([CH:46]=O)C>>[C:14]([C:17]1[CH2:18][N:19]=[C:20]([SH:34]([C:24]2[CH:29]=[CH:28][C:27]([C:46]#[N:44])=[CH:26][CH:25]=2)[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:32])([F:33])[F:31])[CH:25]=2)[C:22]=1[CH3:23])(=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 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 178476583HCID 178476583, compound

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 nm 10% A; wavelength: 220 um; 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 nm 10% A; wavelength: 220 um; injection volume: approx. 550 μl; number of injections: 1)
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a8d0c113ddc41a4baf0ff1859a59941
Source dataset
uspto-grants-2009_07
Patent number
US07566723B2

Reaction notes

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