3-Chlorobenzaldehyde → HCID 178429310, compound

HRID 431238Notes

Reaction equation

HRID 431238 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([OH:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O>C(OC(=O)C)(=O)C>[Cl:10][C:11]1[CH:12]=[C:13](/[CH:14]=[CH:1]/[C:2]2[N:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[N:7]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 114773-ChlorobenzaldehydeHCID 178429343HCID 178429343, compound

Product 1

HCID 178429310HCID 178429310, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
145 °C

Procedure

1.24 g (10 mmol) of 2,4-dimethyl-6-hydroxypyrimidine in acetic anhydride (2.8 ml) were treated at RT with 1.41 g (10 mmol) of 3-chlorobenzaldehyde and the mixture was heated for 5 hours at 145° C. until completion of the reaction according to TLC analysis. The reaction mixture was cooled to RT, the crystalline solid which had formed was filtered off by suction and washed with diethyl ether to give 1.92 g (78%) of the desired (E)-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol as off-white crystals. EI mass spectrum, m/e: 246.1 (M calculated for C13H11ClN2O: 246).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe crystalline solid which had formed
  3. filtrationwas filtered off by suction
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-d3898a4543b04beb8ef550c5b47e90af
Source dataset
uspto-grants-2003_12
Patent number
US06657060B2

Reaction notes

Loading…