Pyridine → 4-{5-Acetyl-6-methyl-3-propionyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

HRID 230285Notes

Reaction equation

HRID 230285 reaction equation
[C:1]([C:4]1[CH:5]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[NH:6][C:7](=[S:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:36](Cl)(=[O:39])[CH2:37][CH3:38]>C1COCC1>[C:1]([C:4]1[CH:5]([C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[N:6]([C:36](=[O:39])[CH2:37][CH3:38])[C:7](=[S:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 115968194-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Product 1

HCID 577624264-{5-Acetyl-6-methyl-3-propionyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile (Example 1; 100 mg, 0.24 mmol) is dissolved in 3 ml THF. After addition of pyridine (21 mg, 0.26 mmol) and propanoyl chloride (22 mg, 0.24 mmol), the reaction mixture is stirred at room temperature overnight and is then quenched with 10 ml water. After extraction with ethyl acetate (2×10 ml), the organic layer is dried with sodium sulfate, and the crude product is purified via flash chromatography on silica gel using a gradient of cyclohexane/ethyl acetate.

Workup

  1. customis then quenched with 10 ml water
  2. extractionAfter extraction with ethyl acetate (2×10 ml)
  3. dry with materialthe organic layer is dried with sodium sulfate
  4. customthe crude product is purified via flash chromatography on silica gel using a gradient of cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-f4234d00428f4ec39b25c5f0a03b47d6
Source dataset
uspto-grants-2009_07
Patent number
US07566723B2

Reaction notes

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