HCID 22125097, compound → HCID 22125033, compound

HRID 1858330Notes

Reaction equation

HRID 1858330 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[NH:4][CH2:5][C:6]1[C:7]([O:14]CC2C=CC(OC)=CC=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[NH:4][CH2:5][C:6]1[C:7](=[O:14])[NH:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1

Participants

3

Reactant 1

HCID 22125097HCID 22125097, compound

Product 1

HCID 22125033HCID 22125033, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5 g (11.5 mmol) of 5-(2,4-dichloroanilinomethyl)-4-(4-methoxy-benzyloxy)-2-methylthiopyrimidine in 30 ml of trifluoroacetic acid was heated at reflux for 20 minutes, cooled and evaporated. The product was purified by flash chromatography on silica gel using ethyl acetate/isohexane in a ratio of 1:2 as eluent. Product-containing fractions were combined and evaporated to give 1.2 g (24%) of 5-[2,4-dichloroanilinomethyl]-2-methylthio-3H-pyrimidin-4-one as a pale yellow solid. [Mass spectrum (ESI) MH+ =316].

Workup

  1. temperatureat reflux for 20 minutes
  2. temperaturecooled
  3. customevaporated
  4. customThe product was purified by flash chromatography on silica gel
  5. customevaporated

Sources & evidence

ORD record
ord-1b359cb1b6c04ac382e67e2b4691ece7
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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